[ CAS No. 154-93-8 ] {[proInfo.proName]}

Name: 154-93-8|1,3-Bis(2-chloroethyl)-1-nitrosourea|97%
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Quality Control of [ 154-93-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 154-93-8 ]

SDS Specification

Alternatived Products of [ 154-93-8 ]

Product Details of [ 154-93-8 ]

CAS No. :	154-93-8	MDL No. :	MFCD00057706
Formula :	C₅H₉Cl₂N₃O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	DLGOEMSEDOSKAD-UHFFFAOYSA-N
M.W :	214.05	Pubchem ID :	2578
Synonyms :	BCNU;bis-chloroethylnitrosourea;BCNU Becenum;FDA 0345;DTI 015;SRI 1720;SK 27702;Nitrumon;NCI-C04773;NSC 409962;Gliadel;BiCNU

Calculated chemistry of [ 154-93-8 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.8
Num. rotatable bonds :	7
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	46.77
TPSA :	61.77 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) :	1.72
Log Po/w (XLOGP3) :	1.53
Log Po/w (WLOGP) :	1.16
Log Po/w (MLOGP) :	0.99
Log Po/w (SILICOS-IT) :	0.66
Consensus Log Po/w :	1.21

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.67
Solubility :	4.59 mg/ml ; 0.0214 mol/l
Class :	Very soluble
Log S (Ali) :	-2.44
Solubility :	0.784 mg/ml ; 0.00366 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.03
Solubility :	2.01 mg/ml ; 0.0094 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.42

Safety of [ 154-93-8 ]

Signal Word:	Danger	Class:	6.1
Precautionary Statements:	P201-P202-P260-P264-P270-P280-P301+P310+P330-P308+P311-P405-P501	UN#:	2811
Hazard Statements:	H300-H341-H350-H360-H370	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 154-93-8 ]

* 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.

Downstream synthetic route of [ 154-93-8 ]

[ 154-93-8 ] Synthesis Path-Downstream 1~15

1
[ 2214-72-4 ]
[ 154-93-8 ]

Yield	Reaction Conditions	Operation in experiment
87%	With formic acid; sodium nitrite; In dichloromethane; water; at 0 - 3℃; for 1h;	Step c. Nitrosation of BCU (2) (0074) NaNO2 (677 g, 9.8 mol) was dissolved in 3.4 L water. To the solution, BCU (2) (282 g, 1.52 mol) and DCM (7 L) were added. The mixture was stirred and cooled to 0 to 3 C. To the tri-phase mixture, formic acid (0.425 L, 11.26 mol) was added dropwise during about 30 minutes. At the end of the addition two clear liquid phases were obtained. The mixture was stirred for additional 30 minutes, and the organic phase was sampled. The reaction was considered complete when Area % HPLC of starting material was less than 0.5%. (0075) Work-up: the two phases were separated and the organic phase was washed twice with water (3.3 L×2). The solution was evaporated to a volume of 1.1 L and then eluted through silica gel, pre-packed with DCM (700 grams high-purity grade silica gel for flash chromatography, pore size 60 , 230-400 mesh ASTM) with final DCM washing. The collected solvent (3.5 L) was evaporated to residue, keeping the internal temperature lower than 10 C. The residue was taken up with pre-cooled MTBE (1.4 L) and the solution was evaporated to residue. The residue was again taken up with pre-cooled MTBE (0.425 L). To this solution, pre-cooled n-heptane (3.5 L) was added, keeping the temperature between 0 and 3 C. (about 30 minutes). At the end of the addition the stirring was continued for 60 minutes at an internal temperature of 0 C. The suspension was filtered, and the solid was washed with pre-cooled n-heptane (0.45 L). The product was dried under vacuum at room temperature until constant weight to provide 283 g BCNU (1). (0076) Yield 87%, HPLC purity 100 Area % (according to USP 37 2014 United States Pharmacopoeia method), NMR title 99.0%. (0077) None of the used solvents (MTBE, DCM, n-heptane) was detected by 1H-NMR.
	In dichloromethane;	EXAMPLE 1 1,3-Bis(2-chloroethyl)-1-nitrosourea A suspension of 1.11 mmole (0.205 g) of 1,3-bis(2-chloroethyl)urea in 8 ml methylene dichloride at -10 C. was saturated with dinitrogen trioxide in 20% excess of theoretical. The heterogeneous mixture gradually changed to a green homogeneous solution. The methylene dichloride was evaporated, and the residue was extracted with 3* 10 ml hexane. Evaporation of the hexane gave 0.1773 g of oil which was the crude BCNU (NSC 409962). The hexane insoluble portion, 0.0649 g, when treated with benzene, gave 0.020 g of 1,3-bis(2-chloroethyl)urea which was benzene insoluble. The benzene solubles were processed through a silica column (1* 10 cm) and 0.0245 g of crude BCNU was obtained.
4.5 kg	With hydrogenchloride; acetic acid; sodium nitrite; In water; at 0 - 30℃; for 1h;Large scale;	1,3-bis(2-chloroethyl)urea (6 kg) was added to the mixture of dilute hydrochloric acid (1.9lit) and acetic acid (24.5 lit) at 25-30C. Cooled the reaction mixture to 0-5C, sodium nitrite(5.59 kg) was slowly added to the reaction mixture in lot-wise at 0-5C and stirred thereaction mixture for 1 hour at the same temperature. The reaction mixture was quenched withpre-cooled water at 0-5C. Cooled the reaction mixture to -15 to -10C and stirred it for 1 hour at the same temperature. Filtered the precipitated solid and washed with water. Dissolved the obtained compound in dichloromethane (24 lit) at 5-10C and stirred for 15 minutes at the same temperature. Both the organic and aqueous layers were separated.Silicagel (3 kg) was added to the organic layer at 5-10C and stirred for 25 minutes at the same temperature. Filtered the reaction mixture through hyflow bed and washed with dichioromethane. Distilled off the solvent completely from the filtrate under reduced pressure and co-distilled with methyl tertiary butyl ether. Pre-cooled Methyl tertiary butyl ether (12 lit) was added to the obtained compound and stirred it for at 0-5C. This reaction mixturewas added to pre-cooled n-heptane (60 lit) at -15 to -10C and stirred the reaction mixture for1 hour at the same temperature. Filtered the precipitated solid and washed with chilled nheptane. Dried the compound at 0-10C under reduced pressure.Yield: 4.5 kg; MR: 30-32C;Purity by HPLC: 99.97%; Impurity at RRT -0.08: 0.01%, Impurity at RRT ?-0.13: Notdetected; 1,3 -bis(2-chloroethyl)urea: 0.02%PXRD of the obtained compound is shown in figure-i and IR shown in figure-2.

12 g		Water (80ml) was taken in a round bottom flask, cooled to 0-5 C, to this sulphuric acid (38g) was added. This was followed by addition of 80 ml of methylene dichloride and lOg of l,3-bis(2-chloroethyl)urea (II). The reaction mixture was stirred while maintaining the temperature at about 0-5C, to this sodium nitrite solution (24g sodium nitrite in 120ml water) was added. The reaction mixture was stirred at the same temperature for 2 hrs, after completion of reaction, layers separated, organic layer was washed with sodium sulfate, and the solvent was distilled off. To the residue a mixture of n-heptane and methyl tertiary butyl ether was added. Reaction mixture was stirred for 1 hr, filtered and the solid thus obtained was dried to give 12g of title compound.
2.04 kg	With formic acid; sodium nitrite; In water; at 0 - 10℃;Large scale;	Add 33.6L of the intermediate obtained in step 2) and formic acid to the reaction kettle, cool the reaction system to 0-10 C, add sodium nitrite / water solution (4.8kg / 9.6L) dropwise, stir the reaction, and after the reaction is completed, add 66.67 L (49.33kg) methyl tertiary ether, the organic phase was washed three times with purified water, concentrated to dryness, to which was added 24L of ethanol and 12L of purified water at room temperature, slowly cooled to -15 , stirred crystallization, filtered, washed with cold water, The crude carmustine was dried.

Reference： [1]Synthesis,2006,p. 2371 - 2375
[2]Patent: US2017/253557,2017,A1 .Location in patent: Paragraph 0074-0077
[3]Journal of medicinal chemistry,1963,vol. 6,p. 669 - 681
[4]Journal of Organic Chemistry,1981,vol. 46,p. 5309 - 5321
[5]Patent: US4028410,1977,A
[6]Patent: WO2017/154019,2017,A1 .Location in patent: Page/Page column 10; 11
[7]Patent: WO2017/178910,2017,A1 .Location in patent: Page/Page column 9
[8]Patent: CN110938018,2020,A .Location in patent: Paragraph 0062-0063; 0066-0082

2
[ 154-93-8 ]
[ 2214-72-4 ]
[ 71353-16-7 ]
[ 2387-20-4 ]
[ 64-17-5 ]
[ 75-04-7 ]

Reference： [1]Journal of Pharmaceutical Sciences,1989,vol. 78,p. 652 - 659

3
[ 154-93-8 ]
[ 64-17-5 ]

Reference： [1]Journal of Organic Chemistry,1982,vol. 47,p. 851 - 856

4
[ 154-93-8 ]
[ 107-21-1 ]
[ 75-07-0 ]
[ 107-07-3 ]

Reference： [1]Journal of Medicinal Chemistry,1980,vol. 23,p. 1245 - 1247

5
[ 154-93-8 ]
[ 407-25-0 ]
1,3-Bis-(2-chloro-ethyl)-1,3-bis-(2,2,2-trifluoro-acetyl)-urea [ No CAS ]

Reference： [1]Analytical Chemistry,1981,vol. 53,p. 1205 - 1208

6
[ 113900-20-2 ]
[ 689-98-5 ]
[ 154-93-8 ]

Reference： [1]Synthesis,1987,p. 1027 - 1029

7
[ 35436-84-1 ]
[ 154-93-8 ]
S-(2-chloroethyl)glutathione [ No CAS ]
(S)-4-[(R)-1-(Carboxymethyl-carbamoyl)-2-mercapto-ethylcarbamoyl]-4-(2-chloro-ethylamino)-butyric acid [ No CAS ]
S-<N-(2-chloroethyl)carbamoyl>glutathione [ No CAS ]
N,S-bis-<N-(2-chloroethyl)carbamoyl>glutathione [ No CAS ]

Reference： [1]Journal of Mass Spectrometry,1995,vol. 30,p. 57 - 68
[2]Journal of Mass Spectrometry,1995,vol. 30,p. 57 - 68

8
[ 35436-84-1 ]
[ 154-93-8 ]
S-(2-chloroethyl)glutathione [ No CAS ]
(S)-4-[(R)-1-(Carboxymethyl-carbamoyl)-2-mercapto-ethylcarbamoyl]-4-(2-chloro-ethylamino)-butyric acid [ No CAS ]
S-<N-(2-chloroethyl)carbamoyl>glutathione [ No CAS ]
(S)-4-Amino-4-[(R)-2-{2-[(R)-2-((S)-2-amino-4-carboxy-butyrylamino)-2-(carboxymethyl-carbamoyl)-ethylsulfanyl]-ethylsulfanyl}-1-(carboxymethyl-carbamoyl)-ethylcarbamoyl]-butyric acid [ No CAS ]

Reference： [1]Journal of Mass Spectrometry,1995,vol. 30,p. 57 - 68

9
[ 154-93-8 ]
S-<N-(2-chloroethyl)carbamoyl>cysteinylglycine [ No CAS ]
(S)-4-Amino-4-[(R)-1-(carboxymethyl-carbamoyl)-2-((E)-2-chloro-vinylcarbamoylsulfanyl)-ethylcarbamoyl]-butyric acid [ No CAS ]
S-<N-(2-chloroethyl)carbamoyl>glutathione [ No CAS ]
(S)-4-Amino-4-[(R)-1-(carboxymethyl-carbamoyl)-2-(4,5-dihydro-oxazol-2-ylsulfanyl)-ethylcarbamoyl]-butyric acid [ No CAS ]

Reference： [1]Journal of Mass Spectrometry,1995,vol. 30,p. 57 - 68

11
[ 154-93-8 ]
[ 3184-13-2 ]
N^δ-nitroso-N^δ-(2-chloroethyl)carbamoyl-L-ornithine; N^δ-(2-chloroethyl)nitrosocarbamoyl-L-ornithine; mixture of [ No CAS ]

Reference： [1]Pharmaceutical Chemistry Journal,1996,vol. 30,p. 227 - 230

12
[ 154-93-8 ]
[ 16682-12-5 ]
N^δ-nitroso-N^δ-(2-chloroethyl)carbamoyl-D-ornithine; N^δ-(2-chloroethyl)nitrosocarbamoyl-D-ornithine; mixture of [ No CAS ]

Reference： [1]Pharmaceutical Chemistry Journal,1996,vol. 30,p. 227 - 230

13
[ 154-93-8 ]
[ 657-27-2 ]
N^ε-nitroso-N^ε-(2-chloroethyl)carbamoyl-L-lysine; N^ε-(2-chloroethyl)nitrosocarbamoyl-L-lysine; mixture of [ No CAS ]

Reference： [1]Pharmaceutical Chemistry Journal,1996,vol. 30,p. 227 - 230

Yield	Reaction Conditions	Operation in experiment
		is administered intravenously as in Test Procedure A, supra, in conjunction with a chemotherapeutic amount of one of the following antineoplastic agents capable of causing emesis: ... nitrogen mustard, cyclophosphamide, dactinomycin, 6-thioguanidine, carmustine, lomustine, methotrexate, 5-fluorouracil, ...
		Chemotherapeutic agents that are bound to monoclonal antibodies of the present invention to drive the cytotoxic activity include the following: ... bryostatin-1, busulfan, camptothecin, 10-hydroxycamptothecin, carmustine, chlorambucil, cisplatin, irinotecan, ...
		Illustrative examples of chemotherapeutic agents which may be conjugated with the antibody of the invention and have a cytotoxic effect include: ... bryostatin-1, busulfan, camptothecin, 10-hydroxycamptothecin, carmustine, chlorambucil, cisplatin, irinotecan, ...

nitrosourea, especially carmustine, lomustine, nimustine

15
[ 154-93-8 ]
diethyl 1-aminoethyl phosphate [ No CAS ]
C₉H₂₀ClN₂O₅P [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In water; at 60℃; for 2h;	5.10 g (0.0279 mol) of diethyl 1-aminoethyl phosphate was placed in a 50 mL reaction flask,4.68 mL of purified water was added, and 2.0 g (0.0093 mol) of carmustine was added at room temperature,At 60 C for 2 h,Then cooled to room temperature,First with 10% dilute hydrochloric acid washing,Dichloromethane extraction,dry,Evaporated under reduced pressure,And then washed with 20 mL of purified water,Extracted with dichloromethane (3 X20 mL)Combined extract,Dried over anhydrous sodium sulfate, filtered and evaporated to dryness under reduced pressure to give the reaction product.

Reference： [1]Patent: CN104119381,2016,B .Location in patent: Paragraph 0044-00445

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H200	Unstable explosive
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H231	May react explosively even in the absence of air at elevated pressure and/or temperature
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H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
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Health hazards
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H300	Fatal if swallowed
H301	Toxic if swallowed
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H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
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. 154-93-8 ] {[proInfo.proName]}

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[ 154-93-8 ] Synthesis Path-Downstream 1~15

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