[ CAS No. 55406-53-6 ] {[proInfo.proName]}

Name: 55406-53-6|3-Iodoprop-2-yn-1-yl butylcarbamate|98%
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SKU: A314951
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Quality Control of [ 55406-53-6 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 55406-53-6 ]

SDS Specification

Alternatived Products of [ 55406-53-6 ]

Product Details of [ 55406-53-6 ]

CAS No. :	55406-53-6	MDL No. :	MFCD00072438
Formula :	C₈H₁₂INO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	WYVVKGNFXHOCQV-UHFFFAOYSA-N
M.W :	281.09	Pubchem ID :	62097
Synonyms :	IPBC;3-Iodo-2-propynyl Butylcarbamate	Chemical Name :	3-Iodoprop-2-yn-1-yl butylcarbamate

Calculated chemistry of [ 55406-53-6 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.62
Num. rotatable bonds :	6
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	56.17
TPSA :	38.33 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.52 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.86
Log Po/w (XLOGP3) :	2.11
Log Po/w (WLOGP) :	1.99
Log Po/w (MLOGP) :	2.0
Log Po/w (SILICOS-IT) :	1.82
Consensus Log Po/w :	2.16

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.52
Solubility :	0.857 mg/ml ; 0.00305 mol/l
Class :	Soluble
Log S (Ali) :	-2.55
Solubility :	0.8 mg/ml ; 0.00285 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.66
Solubility :	0.619 mg/ml ; 0.0022 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	2.52

Safety of [ 55406-53-6 ]

Signal Word:	Danger	Class:	6.1
Precautionary Statements:	P260-P264-P270-P271-P273-P280-P284-P301+P312+P330-P304+P340+P311-P305+P351+P338+P310-P342+P311-P391-P403+P233-P405-P501	UN#:	2811
Hazard Statements:	H302-H318-H331-H334-H372-H410	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 55406-53-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 55406-53-6 ]
Downstream synthetic route of [ 55406-53-6 ]

[ 55406-53-6 ] Synthesis Path-Upstream 1~2

1
[ 57272-05-6 ]
[ 109-73-9 ]
[ 55406-53-6 ]

Yield	Reaction Conditions	Operation in experiment
91%	With hydrogenchloride In Dimethyl ether at 120℃; for 12 h; Industrial scale	1) After weighing 68 kg of 3-propynyl 1-hydroxy-3-propenate and 45 kg of 1-butylamine in 150 L of dimethoxydimethyl ether,After adding to the three reactors, the temperature dropped to 0-5°C, and 16kg concentrated hydrochloric acid solution was slowly added. After the addition, the temperature was increased to 120°C. The reaction time was 12h. After the reaction was completed, the temperature was lowered to 5-10°C, and then the addition was continued. 11kg of sodium iodide was added to warm up to 2530°C, and the reaction was continued for 24h.The resulting reaction solution was distilled under reduced pressure to remove the solvent, and an excess of 800 mL of water was added thereto, followed by stirring for 30 minutes, filtration, and drying to obtain 157 kg of iodopropynyl butylcarbamate.The yield (calculated as 1-butylamine) was 91percent.

Reference： [1] Patent: CN107963983, 2018, A, . Location in patent: Paragraph 0007; 0021-0024

2
[ 76114-73-3 ]
[ 55406-53-6 ]

Yield	Reaction Conditions	Operation in experiment
93.2%	Stage #1: With sodium hydroxide; sodium hypochlorite; sodium iodide In water at 0 - 40℃; for 1.5 h; Stage #2: With acetic acid In water at 40℃; Stage #3: With sodium hydrogensulfite In water at 25 - 59℃;	EXAMPLE I; A reactor was charged with 330g of water which was then cooled to a temperature of 0-8°C. To the cooled water, while stirring was added 3.4 grams of a nonionic surfactant agent MERPOL HCS and 16. 85g of butyl PROPYNYL carbamate while maintaining the temperature between 0-8 C. The reactor was further charged with 8.85g of a 50percent aqueous solution of sodium hydroxide and 16.28 grams of sodium iodide which had been previously dissolved in 50g of water. The temperature was maintained between 5-8°C. The reactor with strong agitation was slowly charged with 70.2g of a 13.6percent solution of sodium hypochlorite while maintaining the reaction mass at a temperature of between 6 and 11 C. The temperature was allowed to ramp up slightly to 15-20°C and the reaction mass was agitated for 90 minutes. The reaction mass was then slowly heated to a temperature of 35-40 C. The ramping up of the temperature was effected at a rate of 0.25 to 0. 75°C per minute. With agitation the pH of the reaction mass was then adjusted to 6.9 with acetic acid. The pH reaction mass was then adjusted to 6.6 with sodium bisulfite. The temperature was then ramped up to 55 to 59°C at a rate of. 25 to. 75°C per minute. When a temperature reached a range of 55-59°C cooling was applied to the reaction mass to ramp the temperature of the reaction mass down to 25-30 C, at a ramp down rate of 0.33-0. 75°C per minute. The reaction mass was then agitated for 10 minutes and then the reaction mass was filtered. The filtration cake was washed twice with 100 mi of water. The cake was then dried at 35 °C to a constant weight. The reaction achieved a yield of 93.5percent of IPBC which assayed at 98.7percent IPBC; EXAMPLE 3; A reactor was charged with 1400 gal of water which was then cooled to a temperature of 0-8 C. To the cooled water, while stirring was added to 87 pounds of a nonionic surfactant agent Merpol HCS and 429 pounds of butyl propynyl carbamate while maintaining the temperature between 0-8 C. The reactor was further charged with 214 pounds of a 50percent aqueous solution of sodium hydroxide and 853 pounds of 50percent sodium iodide solution. The temperature was maintained between 5-8 C. The reactor with strong agitation was slowly charged with 1780 pounds of a 13.6percent solution of sodium of sodium hypochlorite while maintaining the reaction mass at a temperature of between 6 and 11°C. The temperature was allowed to ramp up slightly to 15-20°C and the reaction mass was agitated for 90 minutes. The reaction mass was then slowly heated to a temperature of 35-40°C. The ramping up of the temperature was effected at a rate of 0.25 to 0. 75 C per minute. With agitation the pH of the reaction mass was then adjusted to 6.9 with acetic acid. The pH reaction mass was then adjusted to 6.6 with sodium bisulfite. The temperature was then tamped up to 55 to 59°C at a rate of 0.25 to 0. 75°C per minute. With agitation the pH of the reaction mass was then adjusted to 6.9 with acetic acid. The pH reaction mass was then adjusted to 6.6 with sodium bisulfite. The temperature was then ramped up to 55 to 59°C at a rate of 0.25 to 0. 75°C per minute. When a temperature reached a range of 55-59°C, cooling was applied to the reaction mass to ramp the temperature of the reaction mass down to 25-30°C, at a ramp down rate of 33-75°C per minute. When a temperature reached a range of 55-59°C, cooling was applied to the reaction mass to ramp the temperature of the reaction mass down to 25-30°C, at a ramp down rate of 33-75°C per minute. The reaction mass was then agitated and then the reaction mass was centrifuged with water for 10 minutes. The cake was washed. The cake was then dried at 30-45°C to a constant weight. The reaction achieved a yield of 93.2percent of IPBC which assayed at 98.7percent IPBC
93.5%	Stage #1: With sodium hydroxide; sodium hypochlorite; potassium iodide In water at 0 - 20℃; for 1.5 h; Stage #2: With acetic acid In water Stage #3: With sodium hydrogensulfite In water at 55 - 59℃;	EXAMPLE 2; [0058] The reaction procedure of Example 1 was repeated except that in the iodination step potassium iodide was substituted for sodium iodine. The procedure produced IPBC at a yield of 93.5percent wherein the resulting IPBC assayed at 98.7percent.
93.2%	Stage #1: With sodium hydroxide; sodium hypochlorite; sodium iodide In water at 0 - 20℃; for 1.5 h; Stage #2: With acetic acid In water Stage #3: With sodium hydrogensulfite In water at 55 - 59℃;	EXAMPLE 1; [0050] A reactor was charged with 330 g of water which was then cooled to a temperature of 0-8° C. [0051] To the cooled water, while stirring was added 3.4 grams of a nonionic surfactant agent Merpol HCS and 16.85 g of butyl propynyl carbamate while maintaining the temperature between 0-8° C. [0052] The reactor was further charged with 8.85 g of a 50percent aqueous solution of sodium hydroxide and 16.28 grams of sodium iodide which had been previously dissolved in 50 g of water. The temperature was maintained between 5-8° C. [0053] The reactor with strong agitation was slowly charged with 70.2 g of a 13.6percent solution of sodium hypochlorite while maintaining the reaction mass at a temperature of between 6 and 11° C. [0054] The temperature was allowed to ramp up slightly to 15-20° C. and the reaction mass was agitated for 90 minutes. The reaction mass was then slowly heated to a temperature of 35-40° C. The ramping up of the temperature was effected at a rate of 0.25 to 0.75° C. per minute. [0055] With agitation the pH of the reaction mass was then adjusted to 6.9 with acetic acid. The pH reaction mass was then adjusted to 6.6 with sodium bisulfite. The temperature was then ramped up to 55 to 59° C. at a rate of 0.25 to 0.75° C. per minute. [0056] When a temperature reached a range of 55-59° C. cooling was applied to the reaction mass to ramp the temperature of the reaction mass down to 25-30° C., at a ramp down rate of 0.33-0.75° C. per minute. [0057] The reaction mass was then agitated for 10 minutes and then the reaction mass was filtered. The filtration cake was washed twice with 100 ml of water. The cake was then dried at 35° C. to a constant weight. The reaction achieved a yield of 93.5percent of IPBC which assayed at 98.7percent IPBC.; A reactor was charged with 1400 gal of water which was then cooled to a temperature of 0-8° C. [0060] To the cooled water, while stirring was added to 87 pounds of a nonionic surfactant agent Merpol HCS and 429 pounds of butyl propynyl carbamate while maintaining the temperature between 0-8° C. [0061] The reactor was further charged with 214 pounds of a 50percent aqueous solution of sodium hydroxide and 853 pounds of 50percent sodium iodide solution. The temperature was maintained between 5-8° C. [0062] The reactor with strong agitation was slowly charged with 1780 pounds of a 13.6percent solution of sodium of sodium hypochlorite while maintaining the reaction mass at a temperature of between 6 and 11° C. [0063] The temperature was allowed to ramp up slightly to 15-20° C. and the reaction mass was agitated for 90 minutes. The reaction mass was then slowly heated to a temperature of 35-40° C. The ramping up of the temperature was effected at a rate of 0.25 to 0.75° C. per minute. [0064] With agitation the pH of the reaction mass was then adjusted to 6.9 with acetic acid. The pH reaction mass was then adjusted to 6.6 with sodium bisulfite. The temperature was then tamped up to 55 to 59° C. at a rate of 0.25 to 0.75° C. per minute. [0065] With agitation the pH of the reaction mass was then adjusted to 6.9 with acetic acid. The pH reaction mass was then adjusted to 6.6 with sodium bisulfite. The temperature was then ramped up to 55 to 59° C. at a rate of 0.25 to 0.75° C. per minute. [0066] When a temperature reached a range of 55-59° C., cooling was applied to the reaction mass to ramp the temperature of the reaction mass down to 25-30° C., at a ramp down rate of 33-75° C. per minute. [0067] When a temperature reached a range of 55-59° C., cooling was applied to the reaction mass to ramp the temperature of the reaction mass down to 25-30° C., at a ramp down rate of 33-75° C. per minute. [0068] The reaction mass was then agitated and then the reaction mass was centrifuged with water for 10 minutes. The cake was washed. The cake was then dried at 30-45° C. to a constant weight. The reaction achieved a yield of 93.2percent of IPBC which assayed at 98.7percent IPBC.

83%

With chlorine; sodium iodide; sodium hydroxide In C₁₂-C₁₆-alcohol ethoxylate

Example 1At 5° C., 4.5 g of C₁₂-C₁₆-alcohol ethoxylate, 16.9 g of propargyl butylcarbamate (0.107 mol), 40.7 g of NaI solution (40percent strength, 0.108 mol) and 25.8 g of NaOH solution (50percent strength, 0.322 mol) are introduced as initial charge in 330 g of water. Chlorine (10.3 g, 0.145 mol) is then slowly introduced into the reaction mixture such that the temperature remains below 5° C. When the introduction is complete, the mixture is slowly heated to 20° C. and stirred at this temperature for 4 h. The precipitated solid is then isolated by filtration, washed with water and dried in vacuo.This gives 26.1 g of 3-iodo-2-propynyl N-10 butylcarbamate (purity: 95.4percent (HPLC), polyiodized compounds: <0.1percent (HPLC), yield:83percent).

Reference： [1] Patent: WO2005/16871, 2005, A1, . Location in patent: Page/Page column 10-11; 12-13
[2] Patent: US2005/33083, 2005, A1, . Location in patent: Page/Page column 3-4
[3] Patent: US2005/33083, 2005, A1, . Location in patent: Page/Page column 3-4
[4] Patent: US2012/330051, 2012, A1, . Location in patent: Page/Page column 2
[5] Patent: US5183927, 1993, A,
[6] Patent: US5183927, 1993, A,

[ 55406-53-6 ] Synthesis Path-Downstream 1~4

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 5 The same procedure as described in Example 1 was repeated, except that the reaction temperature was maintained at 20 C. Thus, there was obtained 13.6 g of 1-iodoprop-1-yn-3-yl N-n-butylcarbamate. This product had a melting point of 65-67 C., its yield was 96.8 mole %, and no impurity was detected by its purity analysis.
		EXAMPLE 6 The same procedure as described in Example 1 was repeated, except that a mixture of 60 g of ethanol and 20 g of water was used in place of 80 g of methanol. Thus, there was obtained 13.8 g of 1-iodoprop-1-yn-3-yl N-n-butylcarbamate. This product had a melting point of 65-67 C., its yield was 98.3 mole %, and no impurity was detected by its purity analysis.
		COMPARATIVE EXAMPLE 1 The same procedure as described in Example 1 was repeated, except that 6.66 g (0.026 mole) of iodine was used in place of 28% iodine monochloride (equivalent to 0.053 mole). Thus, there was obtained 7.3 g of 1-iodoprop-1-yn-3-yl N-n-butylcarbamate (in a yield of 52.0 mole %). Its purity analysis revealed the presence of 1.2% of polyiodinated products (impurities).

		COMPARATIVE EXAMPLE 2 The same procedure as described in Example 1 was repeated, except that the reaction temperature was maintained at 50 C. Thus, there was obtained 11.6 g of 1-iodoprop-1-yn-3-yl N-n-butylcarbamate (in a yield of 82.3 mole %). Its purity analysis revealed the presence of 1.5% of polyiodinated products (impurities).
		COMPARATIVE EXAMPLE 3 The same procedure as described in Example 1 was repeated, except that 13.20 g (0.52 mole) of iodine was used in place of 28% iodine monochloride (equivalent to 0.053 mole). Thus, there was obtained 11.9 g of 1-iodoprop-1-yn-3-yl N-n-butylcarbamate (in a yield of 84.7 mole %). Its purity analysis revealed the presence of 2.5% of polyiodinated products (impurities).
		organotin compounds, such as tributyltin oxide and tributyltin benozoate ... 2-thiocyanomethyl-thiobenzothiazole copper naphthenate copper-8-oxyquinoline p-chlorophenyl-3-propargyl-formal 3-iodo-2-propynyl-butyl-carbamate N-dichlorofluoromethylthio-N',N'-dimethyl-N-phenylsulfuric acid diamide.

2
[ 76114-73-3 ]
[ 55406-53-6 ]

Yield	Reaction Conditions	Operation in experiment
93.2 - 93.5%		EXAMPLE I; A reactor was charged with 330g of water which was then cooled to a temperature of 0-8C. To the cooled water, while stirring was added 3.4 grams of a nonionic surfactant agent MERPOL HCS and 16. 85g of butyl PROPYNYL carbamate while maintaining the temperature between 0-8 C. The reactor was further charged with 8.85g of a 50% aqueous solution of sodium hydroxide and 16.28 grams of sodium iodide which had been previously dissolved in 50g of water. The temperature was maintained between 5-8C. The reactor with strong agitation was slowly charged with 70.2g of a 13.6% solution of sodium hypochlorite while maintaining the reaction mass at a temperature of between 6 and 11 C. The temperature was allowed to ramp up slightly to 15-20C and the reaction mass was agitated for 90 minutes. The reaction mass was then slowly heated to a temperature of 35-40 C. The ramping up of the temperature was effected at a rate of 0.25 to 0. 75C per minute. With agitation the pH of the reaction mass was then adjusted to 6.9 with acetic acid. The pH reaction mass was then adjusted to 6.6 with sodium bisulfite. The temperature was then ramped up to 55 to 59C at a rate of. 25 to. 75C per minute. When a temperature reached a range of 55-59C cooling was applied to the reaction mass to ramp the temperature of the reaction mass down to 25-30 C, at a ramp down rate of 0.33-0. 75C per minute. The reaction mass was then agitated for 10 minutes and then the reaction mass was filtered. The filtration cake was washed twice with 100 mi of water. The cake was then dried at 35 C to a constant weight. The reaction achieved a yield of 93.5% of IPBC which assayed at 98.7% IPBC; EXAMPLE 3; A reactor was charged with 1400 gal of water which was then cooled to a temperature of 0-8 C. To the cooled water, while stirring was added to 87 pounds of a nonionic surfactant agent Merpol HCS and 429 pounds of <strong>[76114-73-3]butyl propynyl carbamate</strong> while maintaining the temperature between 0-8 C. The reactor was further charged with 214 pounds of a 50% aqueous solution of sodium hydroxide and 853 pounds of 50% sodium iodide solution. The temperature was maintained between 5-8 C. The reactor with strong agitation was slowly charged with 1780 pounds of a 13.6% solution of sodium of sodium hypochlorite while maintaining the reaction mass at a temperature of between 6 and 11C. The temperature was allowed to ramp up slightly to 15-20C and the reaction mass was agitated for 90 minutes. The reaction mass was then slowly heated to a temperature of 35-40C. The ramping up of the temperature was effected at a rate of 0.25 to 0. 75 C per minute. With agitation the pH of the reaction mass was then adjusted to 6.9 with acetic acid. The pH reaction mass was then adjusted to 6.6 with sodium bisulfite. The temperature was then tamped up to 55 to 59C at a rate of 0.25 to 0. 75C per minute. With agitation the pH of the reaction mass was then adjusted to 6.9 with acetic acid. The pH reaction mass was then adjusted to 6.6 with sodium bisulfite. The temperature was then ramped up to 55 to 59C at a rate of 0.25 to 0. 75C per minute. When a temperature reached a range of 55-59C, cooling was applied to the reaction mass to ramp the temperature of the reaction mass down to 25-30C, at a ramp down rate of 33-75C per minute. When a temperature reached a range of 55-59C, cooling was applied to the reaction mass to ramp the temperature of the reaction mass down to 25-30C, at a ramp down rate of 33-75C per minute. The reaction mass was then agitated and then the reaction mass was centrifuged with water for 10 minutes. The cake was washed. The cake was then dried at 30-45C to a constant weight. The reaction achieved a yield of 93.2% of IPBC which assayed at 98.7% IPBC
93.5%		EXAMPLE 2; [0058] The reaction procedure of Example 1 was repeated except that in the iodination step potassium iodide was substituted for sodium iodine. The procedure produced IPBC at a yield of 93.5% wherein the resulting IPBC assayed at 98.7%.
93.2 - 93.5%		EXAMPLE 1; [0050] A reactor was charged with 330 g of water which was then cooled to a temperature of 0-8 C. [0051] To the cooled water, while stirring was added 3.4 grams of a nonionic surfactant agent Merpol HCS and 16.85 g of <strong>[76114-73-3]butyl propynyl carbamate</strong> while maintaining the temperature between 0-8 C. [0052] The reactor was further charged with 8.85 g of a 50% aqueous solution of sodium hydroxide and 16.28 grams of sodium iodide which had been previously dissolved in 50 g of water. The temperature was maintained between 5-8 C. [0053] The reactor with strong agitation was slowly charged with 70.2 g of a 13.6% solution of sodium hypochlorite while maintaining the reaction mass at a temperature of between 6 and 11 C. [0054] The temperature was allowed to ramp up slightly to 15-20 C. and the reaction mass was agitated for 90 minutes. The reaction mass was then slowly heated to a temperature of 35-40 C. The ramping up of the temperature was effected at a rate of 0.25 to 0.75 C. per minute. [0055] With agitation the pH of the reaction mass was then adjusted to 6.9 with acetic acid. The pH reaction mass was then adjusted to 6.6 with sodium bisulfite. The temperature was then ramped up to 55 to 59 C. at a rate of 0.25 to 0.75 C. per minute. [0056] When a temperature reached a range of 55-59 C. cooling was applied to the reaction mass to ramp the temperature of the reaction mass down to 25-30 C., at a ramp down rate of 0.33-0.75 C. per minute. [0057] The reaction mass was then agitated for 10 minutes and then the reaction mass was filtered. The filtration cake was washed twice with 100 ml of water. The cake was then dried at 35 C. to a constant weight. The reaction achieved a yield of 93.5% of IPBC which assayed at 98.7% IPBC.; A reactor was charged with 1400 gal of water which was then cooled to a temperature of 0-8 C. [0060] To the cooled water, while stirring was added to 87 pounds of a nonionic surfactant agent Merpol HCS and 429 pounds of <strong>[76114-73-3]butyl propynyl carbamate</strong> while maintaining the temperature between 0-8 C. [0061] The reactor was further charged with 214 pounds of a 50% aqueous solution of sodium hydroxide and 853 pounds of 50% sodium iodide solution. The temperature was maintained between 5-8 C. [0062] The reactor with strong agitation was slowly charged with 1780 pounds of a 13.6% solution of sodium of sodium hypochlorite while maintaining the reaction mass at a temperature of between 6 and 11 C. [0063] The temperature was allowed to ramp up slightly to 15-20 C. and the reaction mass was agitated for 90 minutes. The reaction mass was then slowly heated to a temperature of 35-40 C. The ramping up of the temperature was effected at a rate of 0.25 to 0.75 C. per minute. [0064] With agitation the pH of the reaction mass was then adjusted to 6.9 with acetic acid. The pH reaction mass was then adjusted to 6.6 with sodium bisulfite. The temperature was then tamped up to 55 to 59 C. at a rate of 0.25 to 0.75 C. per minute. [0065] With agitation the pH of the reaction mass was then adjusted to 6.9 with acetic acid. The pH reaction mass was then adjusted to 6.6 with sodium bisulfite. The temperature was then ramped up to 55 to 59 C. at a rate of 0.25 to 0.75 C. per minute. [0066] When a temperature reached a range of 55-59 C., cooling was applied to the reaction mass to ramp the temperature of the reaction mass down to 25-30 C., at a ramp down rate of 33-75 C. per minute. [0067] When a temperature reached a range of 55-59 C., cooling was applied to the reaction mass to ramp the temperature of the reaction mass down to 25-30 C., at a ramp down rate of 33-75 C. per minute. [0068] The reaction mass was then agitated and then the reaction mass was centrifuged with water for 10 minutes. The cake was washed. The cake was then dried at 30-45 C. to a constant weight. The reaction achieved a yield of 93.2% of IPBC which assayed at 98.7% IPBC.

83%	With chlorine; sodium iodide; sodium hydroxide; In C12-C16-alcohol ethoxylate;Product distribution / selectivity;	Example 1At 5 C., 4.5 g of C12-C16-alcohol ethoxylate, 16.9 g of <strong>[76114-73-3]propargyl butylcarbamate</strong> (0.107 mol), 40.7 g of NaI solution (40% strength, 0.108 mol) and 25.8 g of NaOH solution (50% strength, 0.322 mol) are introduced as initial charge in 330 g of water. Chlorine (10.3 g, 0.145 mol) is then slowly introduced into the reaction mixture such that the temperature remains below 5 C. When the introduction is complete, the mixture is slowly heated to 20 C. and stirred at this temperature for 4 h. The precipitated solid is then isolated by filtration, washed with water and dried in vacuo.This gives 26.1 g of 3-iodo-2-propynyl N-10 butylcarbamate (purity: 95.4% (HPLC), polyiodized compounds: <0.1% (HPLC), yield:83%).
	With sodium hydroxide; sodium chloride; Iodine monochloride; In methanol;	EXAMPLE 1 A reactor (having a capacity of 200 ml and fitted with a condenser and a stirrer) was charged with 7.75 g (0.050 mole) of <strong>[76114-73-3]prop-1-yn-3-yl N-n-butylcarbamate</strong> and 80 g of methanol, followed by the addition of 8.3 g (equivalent to 0.073 mole) of a 35% aqueous solution of sodium hydroxide. While this solution was cooled to and maintained at 10 C., 30.5 g of a 15% aqueous solution of sodium chloride containing 28% iodine monochloride (equivalent to 0.053 mole) was added thereto over a period of 20 minutes. Furthermore, the solution was reacted at 15 C. for 2 hours. Thereafter, the reacted solution was neutralized with hydrochloric acid and extracted with 40 g of toluene. The reacted solution was further extracted five times with toluene and the combined toluene extract was dried over anhydrous magnesium sulfate. Finally, the toluene was removed by evaporation under reduced pressure to obtain 13.8 g of 1-iodo<strong>[76114-73-3]prop-1-yn-3-yl N-n-butylcarbamate</strong>. This product had a melting point of 65-67 C., its yield was 98.3 mole %, and no impurity was detected by its purity analysis.
	With sodium hydroxide; sodium hypochlorite; iodine; In methanol;	COMPARATIVE EXAMPLE 4 A reactor (having a capacity of 200 ml and fitted with a condenser and a stirrer) was charged with 7.75 g (0.050 mole) of <strong>[76114-73-3]prop-1-yn-3-yl N-n-butylcarbamate</strong> and 80 g of methanol, followed by the addition of 8.3 g (equivalent to 0.073 mole) of a 35% aqueous solution of sodium hydroxide. While this solution was cooled to and maintained at 10 C., 6.73 g (equivalent to 0.027 mole) of iodine was added thereto. After 20.5 g of a 6% aqueous solution of sodium hypochlorite was subsequently added thereto, the solution was reacted for 2 hours while its temperature was maintained at 10 C. Thereafter, the reacted solution was neutralized with hydrochloric acid and extracted with 40 g of toluene. The reacted solution was further extracted five times with toluene and the combined toluene extract was dried over anhydrous magnesium sulfate. Finally, the toluene was removed by evaporation under reduced pressure to obtain 11.4 g of 1-iodo<strong>[76114-73-3]prop-1-yn-3-yl N-n-butylcarbamate</strong>. Its yield was 81.2 mole %, and its purity analysis revealed the presence of 0.5% of polyiodinated products (impurities).

Reference： [1]Patent: WO2005/16871,2005,A1 .Location in patent: Page/Page column 10-11; 12-13
[2]Patent: US2005/33083,2005,A1 .Location in patent: Page/Page column 3-4
[3]Patent: US2005/33083,2005,A1 .Location in patent: Page/Page column 3-4
[4]Patent: US2012/330051,2012,A1 .Location in patent: Page/Page column 2
[5]Patent: US5183927,1993,A
[6]Patent: US5183927,1993,A

Yield	Reaction Conditions	Operation in experiment
	With Octasoligen-Cobalt 8; In 2-Propanol, 1-<2-(2-methoxy-1-methylethoxy)-1-methylethoxy>-; at 40℃; for 336.0h;Reactivity;	EXAMPLESA solution is prepared in Dowanol TPM (tripropylene glycol methyl ether), containing 10% by weight of iodopropargyl butylcarbamate, 5% by weight of Octasoligen-Cobalt 8 (Borchers, Langenfeld, Germany) and 5% by weight of the stabilizer specified in Table 1. The compositions are stored at 40 C. The amount of <strong>[55406-53-6]IPBC</strong> was determined by means of HPLC at the beginning and after two weeks.
	With 2-(2-Hydroxy-5-methylphenyl)benzotriazole; In 2-Propanol, 1-<2-(2-methoxy-1-methylethoxy)-1-methylethoxy>-; at 40℃; for 336.0h;Reactivity;	EXAMPLESA solution is prepared in Dowanol TPM (tripropylene glycol methyl ether), containing 10% by weight of iodopropargyl butylcarbamate, 5% by weight of Octasoligen-Cobalt 8 (Borchers, Langenfeld, Germany) and 5% by weight of the stabilizer specified in Table 1. The compositions are stored at 40 C. The amount of <strong>[55406-53-6]IPBC</strong> was determined by means of HPLC at the beginning and after two weeks.
	With 2-(5-tert-butyl-2-hydroxyphenyl)benzotriazole; In 2-Propanol, 1-<2-(2-methoxy-1-methylethoxy)-1-methylethoxy>-; at 40℃; for 336.0h;Reactivity (does not react);	EXAMPLESA solution is prepared in Dowanol TPM (tripropylene glycol methyl ether), containing 10% by weight of iodopropargyl butylcarbamate, 5% by weight of Octasoligen-Cobalt 8 (Borchers, Langenfeld, Germany) and 5% by weight of the stabilizer specified in Table 1. The compositions are stored at 40 C. The amount of <strong>[55406-53-6]IPBC</strong> was determined by means of HPLC at the beginning and after two weeks.

	With Cyasorb UV 5411; In 2-Propanol, 1-<2-(2-methoxy-1-methylethoxy)-1-methylethoxy>-; at 40℃; for 336.0h;Reactivity;	EXAMPLESA solution is prepared in Dowanol TPM (tripropylene glycol methyl ether), containing 10% by weight of iodopropargyl butylcarbamate, 5% by weight of Octasoligen-Cobalt 8 (Borchers, Langenfeld, Germany) and 5% by weight of the stabilizer specified in Table 1. The compositions are stored at 40 C. The amount of <strong>[55406-53-6]IPBC</strong> was determined by means of HPLC at the beginning and after two weeks.
	With 2-(2H-benzo[d][1,2,3]triazol-2-yl)-4-(2-hydroxyethyl)phenol; In 2-Propanol, 1-<2-(2-methoxy-1-methylethoxy)-1-methylethoxy>-; at 40℃; for 336.0h;Reactivity;	EXAMPLESA solution is prepared in Dowanol TPM (tripropylene glycol methyl ether), containing 10% by weight of iodopropargyl butylcarbamate, 5% by weight of Octasoligen-Cobalt 8 (Borchers, Langenfeld, Germany) and 5% by weight of the stabilizer specified in Table 1. The compositions are stored at 40 C. The amount of <strong>[55406-53-6]IPBC</strong> was determined by means of HPLC at the beginning and after two weeks.
	With 3-(2H-benzo[d][1,2,3]triazol-2-yl)-4-hydroxyphenethyl methacrylate; In 2-Propanol, 1-<2-(2-methoxy-1-methylethoxy)-1-methylethoxy>-; at 40℃; for 336.0h;Reactivity;	EXAMPLESA solution is prepared in Dowanol TPM (tripropylene glycol methyl ether), containing 10% by weight of iodopropargyl butylcarbamate, 5% by weight of Octasoligen-Cobalt 8 (Borchers, Langenfeld, Germany) and 5% by weight of the stabilizer specified in Table 1. The compositions are stored at 40 C. The amount of <strong>[55406-53-6]IPBC</strong> was determined by means of HPLC at the beginning and after two weeks.

4
[ 57272-05-6 ]
[ 109-73-9 ]
[ 55406-53-6 ]

Yield	Reaction Conditions	Operation in experiment
91%	With hydrogenchloride; In Dimethyl ether; at 120℃; for 12.0h;Industrial scale;	1) After weighing 68 kg of 3-propynyl 1-hydroxy-3-propenate and 45 kg of 1-butylamine in 150 L of dimethoxydimethyl ether,After adding to the three reactors, the temperature dropped to 0-5C, and 16kg concentrated hydrochloric acid solution was slowly added. After the addition, the temperature was increased to 120C. The reaction time was 12h. After the reaction was completed, the temperature was lowered to 5-10C, and then the addition was continued. 11kg of sodium iodide was added to warm up to 2530C, and the reaction was continued for 24h.The resulting reaction solution was distilled under reduced pressure to remove the solvent, and an excess of 800 mL of water was added thereto, followed by stirring for 30 minutes, filtration, and drying to obtain 157 kg of iodopropynyl butylcarbamate.The yield (calculated as 1-butylamine) was 91%.

Reference： [1]Patent: CN107963983,2018,A .Location in patent: Paragraph 0007; 0021-0024

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H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 55406-53-6 ] {[proInfo.proName]}

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[ 55406-53-6 ] Synthesis Path-Upstream 1~2

[ 55406-53-6 ] Synthesis Path-Downstream 1~4

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Alkynes

Aliphatic Chain Hydrocarbons

Amides

Amines

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[ 55406-53-6 ]