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Quality Control of Boc-N-Me-DL-Val-OH Purity: 95% SDS Specification

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Product Details of Boc-N-Me-DL-Val-OH

CAS No. :	13850-91-4
Formula :	C₁₁H₂₁NO₄
M.W :	231.29
SMILES Code :	CC(C)C(C(O)=O)N(C(OC(C)(C)C)=O)C
MDL No. :	MFCD00153317

Safety of Boc-N-Me-DL-Val-OH

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of Boc-N-Me-DL-Val-OH

* 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 [ 13850-91-4 ]

[ 13850-91-4 ] Synthesis Path-Downstream 1~35

1
[ 124-38-9 ]
[ 140175-19-5 ]
[ 13850-91-4 ]

References: [1]Journal of Organic Chemistry,1992,vol. 57,p. 2220 - 2222.

2
[ 2016-04-8 ]
[ 13850-91-4 ]
[ 89536-87-8 ]

References: [1]Helvetica Chimica Acta,1983,vol. 66,p. 2672 - 2702.

3
[ 13850-91-4 ]
[ 88930-14-7 ]

References: [1]Journal of Organic Chemistry,1986,vol. 51,p. 3350 - 3354.

4
[ 22838-58-0 ]
[ 74-88-4 ]
[ 13850-91-4 ]

Yield	Reaction Conditions	Operation in experiment
84%		To N-Boc D-valine (5 g, 11.5 mmol) at 0 C in THF (69 mL, 0.35 M) is added MeI (11.45 mL, 8 eq). NaH (60% dispersion in mineral oil, 2.76 g, 3eq) is then added carefully to the stirring solution portionwise. The mixturewas allowed to stir vigorously overnight at room temperature before beingdiluted with Et2O (70 mL) and quenched slowly with H2O (50 mL) at 0 C.The layers were separated and the aqueous layer extracted twice with Et2O(2 x 30 mL). The aqueous layer was brought to ~pH 2 with the dropwise addition of conc. HCl(checking the pH by spotting the aqueous layer onto pH paper) and extracted with EtOAc (4 x100 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered, andconcentrated in vacuo. The resulting oil (4.46 g, 84% yield) was sufficiently pure for the nextstep. If desired, an analytical sample could be obtained as a white fluffy solid after flash columnchromatography (silica gel, 3%-5% MeOH/DCM). The use of only 3 eq of MeI in a similarprocedure resulted in the appearance of starting material at the end of the reaction, presumablydue to competitive precipitation of the disodium salt.3

References: [1]Organic and Biomolecular Chemistry,2016,vol. 14,p. 2090 - 2111.
[2]Helvetica Chimica Acta,2012,vol. 95,p. 973 - 982.
[3]Tetrahedron Letters,2012,vol. 53,p. 4077 - 4079.
[4]Organic and Biomolecular Chemistry,2017,vol. 15,p. 1140 - 1150.
[5]Tetrahedron,1995,vol. 51,p. 10653 - 10662.
[6]Marine Drugs,2012,vol. 10,p. 1307 - 1320.
[7]Organic and Biomolecular Chemistry,2012,vol. 10,p. 7027 - 7030.
[8]Current Medicinal Chemistry,2013,vol. 20,p. 1183 - 1194.

5
[ 13734-34-4 ]
[ 52574-08-0 ]
[ 13850-91-4 ]
(S)-2-((R)-2-[3-(Acetylamino-methylsulfanyl)-propionyl]-methyl-amino}-3-methyl-butyrylamino)-3-phenyl-propionic acid [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,1997,vol. 5,p. 115 - 124.

6
[ 115962-35-1 ]
[ 52574-08-0 ]
[ 13850-91-4 ]
(S)-2-((R)-2-[3-(Acetylamino-methylsulfanyl)-propionyl]-methyl-amino}-3-methyl-butyryl)-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,1997,vol. 5,p. 115 - 124.

7
[ 13850-91-4 ]
[ 188399-96-4 ]
(S)-2-({(S)-2-[(R)-2-(tert-Butoxycarbonyl-methyl-amino)-3-methyl-butyryl]-1,2,3,4-tetrahydro-isoquinolin-3-ylmethyl}-amino)-4-methylsulfanyl-butyric acid methyl ester [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,1997,vol. 5,p. 115 - 124.

8
[ 13850-91-4 ]
C₁₇H₃₉NO₃P₂ [ No CAS ]
diethyl (N-t-butoxycarbonyl-N-mehyl-D-valyl)aminomethylphosphonate [ No CAS ]

References: [1]Tetrahedron,2000,vol. 56,p. 3755 - 3761.

9
[ 13850-91-4 ]
[ 639457-63-9 ]
2-[2-(tert-butoxycarbonyl-methyl-amino)-3-methyl-butyrylamino]-3-[2-(3-methyl-but-2-enyl)-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-propionic acid methyl ester [ No CAS ]

References: [1]Tetrahedron,2003,vol. 59,p. 8931 - 8946.

10
[ 17407-56-6 ]
[ 13850-91-4 ]
(R)-2-(tert-Butoxycarbonyl-methyl-amino)-3-methyl-butyric acid (R)-1-carboxy-2-methyl-propyl ester [ No CAS ]

References: [1]Organic Letters,2004,vol. 6,p. 4615 - 4617.

11
[ 17407-55-5 ]
[ 13850-91-4 ]
(R)-2-(tert-Butoxycarbonyl-methyl-amino)-3-methyl-butyric acid (S)-1-carboxy-2-methyl-propyl ester [ No CAS ]

References: [1]Organic Letters,2004,vol. 6,p. 4615 - 4617.

12
[ 640-68-6 ]
[ 24424-99-5 ]
[ 74-88-4 ]
[ 13850-91-4 ]

References: [1]Organic Letters,2004,vol. 6,p. 4615 - 4617.

13
[ 104-15-4 ]
[ 13850-91-4 ]
[ 100-51-6 ]
H-N-Me-D-Val-OBzl p-toluenesulfonic acid salt [ No CAS ]

References: [1]Synthetic Communications,2005,vol. 35,p. 1795 - 1802.

14
[ 789428-88-2 ]
[ 13850-91-4 ]
[ 863781-54-8 ]

References: [1]Organic Letters,2005,vol. 7,p. 3481 - 3484.
[2]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 5625 - 5631.
[3]Journal of Medicinal Chemistry,2008,vol. 51,p. 530 - 544.

15
[ 915374-30-0 ]
[ 13850-91-4 ]
[ 863781-56-0 ]

References: [1]Organic Letters,2005,vol. 7,p. 3481 - 3484.
[2]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 5625 - 5631.

16
[ 38155-18-9 ]
[ 13850-91-4 ]
[ 909108-64-1 ]

References: [1]Journal of Organic Chemistry,2007,vol. 72,p. 1980 - 2002.
[2]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 5625 - 5631.
[3]Journal of Medicinal Chemistry,2008,vol. 51,p. 530 - 544.

17
2-(benzothiazole-2-sulfonylamino)-3-(4-tert-butoxy-phenyl)-propionic acid [ No CAS ]
[ 811867-17-1 ]
[ 53308-95-5 ]
[ 13850-91-4 ]
9-(4-hydroxy-benzyl)-12-isopropyl-11-methyl-15-propyl-6,7,8,9,11,12,14,15,17,18,19,20-dodecahydro-5-oxa-8,11,14,17-tetraaza-benzocyclooctadecene-10,13,16-trione [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 7190 - 7197.

18
[ 13850-91-4 ]
[ 812788-74-2 ]

References: [1]Organic Letters,2004,vol. 6,p. 4615 - 4617.

19
[ 13850-91-4 ]
(3R,6R)-3,6-diisopropyl-4-methyl-2,5-morpholinedione [ No CAS ]

References: [1]Organic Letters,2004,vol. 6,p. 4615 - 4617.

20
[ 13850-91-4 ]
[ 103478-61-1 ]

References: [1]Journal of Organic Chemistry,1986,vol. 51,p. 3350 - 3354.

21
[ 13850-91-4 ]
Fmoc-MeLeu-D-MeVal-O-t-Bu [ No CAS ]

References: [1]Journal of Organic Chemistry,1986,vol. 51,p. 3350 - 3354.

22
[ 13850-91-4 ]
Boc-D-Ala-MeLeu-D-MeLeu-D-MeVal-OH [ No CAS ]

References: [1]Helvetica Chimica Acta,1983,vol. 66,p. 2672 - 2702.

23
[ 13850-91-4 ]
Boc-D-Ala-MeLeu-L-MeLeu-D-MeVal-OH [ No CAS ]

References: [1]Helvetica Chimica Acta,1983,vol. 66,p. 2672 - 2702.

24
[ 13850-91-4 ]
Boc-D-Ala-MeLeu-D/L-MeLeu-D-MeVal-OBzl [ No CAS ]

References: [1]Helvetica Chimica Acta,1983,vol. 66,p. 2672 - 2702.

25
[ 468-36-0 ]
[ 13850-91-4 ]
C₃₄H₅₇N₃O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; dichloromethane; at 20℃;	Example 61 Methyl-{2-methyl-1-[methyl-(2,3,11a-trimethyl-2,3,3a,4,5,5a,5b,6,8,9,10,11,11a, 11b,12,13-hexadecahydro-1H-2-aza-pentaleno[1,6a-a]phenanthren-9-yl)-carbamoyl]-propyl}-carbamic acid tert-butyl ester; A mixture of compound 7B (240 mg, 0.702 mmol), Boc-N-methyl-D-valine (176 mg, 0.762 mmol), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (208 mg, 1.085 mmol), 1-hydroxybenzotriazole (146 mg, 1.085 mmol), dichloromethane (5 mL) and THF (2.5 mL) was stirred at room temperature overnight. The solvent was evaporated under reduced pressure and the residue was dissolved in minimum amount of dichloromethane and purified on silica gel column, which was eluted with 0.5% ammonium hydroxide and 5% methanol in dichloromethane to give the desired product (282 mg, 72% yield). 1H NMR (CDCl3): delta 0.89 (m, 12 H) 1.00-1.40 (m, 11 H) 1.46 (m, 9 H) 1.50-2.60 (m, 12 H) 2.74 (d, 3 H) 2.85 (d, 3 H) 2.94 (d, 3 H) 3.91 (m, 1 H) 4.34 (m, 1 H) 4.65 (m, 1 H) 5.38 (m,1 H). MS: (M+H)+=556.

References: [1]Patent: US2005/227953,2005,A1 .Location in patent: Page/Page column 36.
[2]Journal of Medicinal Chemistry,2008,vol. 51,p. 5423 - 5430.

26
[ 468-36-0 ]
[ 13850-91-4 ]
methyl-{2-methyl-1-[methyl-(2,3,11a-trimethyl-2,3,3a,4,5,5a,5b,6,8,9,10,11,11a,11b,12,13-hexadecahydro-1H-2-aza-pentaleno[1,6a-a]phenanthren-9-yl)-carbamoyl]-propyl}-carbamic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; dichloromethane; at 20℃;	A mixture of compound 7B (240 mg, 0.702 mmol), Boc-N-methyl-D-valine (176 mg, 0.762 mmol), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (208 mg, 1.085 mmol), 1-hydroxybenzotriazole (146 mg, 1.085 mmol), dichloromethane (5 mL) and THF (2.5 mL) was stirred at room temperature overnight. The solvent was evaporated under reduced pressure and the residue was d issolved in minimum amount of dichloromethane and purified on silica gel column, which was eluted with 0.5% ammonium hydroxide and 5% methanol in dichloromethane to give the desired product (282 mg, 72% yield). ¹H NMR (CDC13): 8 0.89 (m, 12 H) 1.00-1.40 (m, 11 H) 1.46 (m, 9 H) 1.50-2.60 (m, 12 H) 2.74 (d, 3 H) 2.85 (d, 3 H) 2.94 (d, 3 H) 3.91 (m, 1 H) 4.34 (m, 1 H) 4.65 (m, 1 H) 5.38 (m, 1 H). MS: (M+H)+= 556.

References: [1]Patent: WO2005/100377,2005,A1 .Location in patent: Page/Page column 24; 79; 80.

27
[ 13850-91-4 ]
[ 1334672-02-4 ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 6432 - 6442.

28
[ 13850-91-4 ]
[ 1334671-80-5 ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 6432 - 6442.

29
[ 13850-91-4 ]
[ 543-27-1 ]
C₁₆H₂₉NO₆ [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 6432 - 6442.

30
[ 186581-53-3 ]
[ 13850-91-4 ]
methyl N-Methyl-D-valinate [ No CAS ]

References: [1]Marine Drugs,2012,vol. 10,p. 1307 - 1320.

31
[ 13850-91-4 ]
Boc-L-Lys-D-N-MeVal-L-N-MeAla-OH [ No CAS ]

References: [1]Marine Drugs,2012,vol. 10,p. 1307 - 1320.
[2]Helvetica Chimica Acta,2012,vol. 95,p. 973 - 982.
[3]Helvetica Chimica Acta,2012,vol. 95,p. 973 - 982.

32
[ 13850-91-4 ]
[ 1268729-68-5 ]

References: [1]Marine Drugs,2012,vol. 10,p. 1307 - 1320.
[2]Helvetica Chimica Acta,2012,vol. 95,p. 973 - 982.
[3]Helvetica Chimica Acta,2012,vol. 95,p. 973 - 982.

33
[ 13850-91-4 ]
[ 1268729-65-2 ]

References: [1]Marine Drugs,2012,vol. 10,p. 1307 - 1320.
[2]Helvetica Chimica Acta,2012,vol. 95,p. 973 - 982.
[3]Helvetica Chimica Acta,2012,vol. 95,p. 973 - 982.

34
[ 13850-91-4 ]
[ 1268729-57-2 ]

References: [1]Marine Drugs,2012,vol. 10,p. 1307 - 1320.
[2]Helvetica Chimica Acta,2012,vol. 95,p. 973 - 982.

35
[ 13850-91-4 ]
[ 1268729-63-0 ]

References: [1]Marine Drugs,2012,vol. 10,p. 1307 - 1320.
[2]Helvetica Chimica Acta,2012,vol. 95,p. 973 - 982.
[3]Helvetica Chimica Acta,2012,vol. 95,p. 973 - 982.

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
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P233	Keep container tightly closed.
P234	Keep only in original container.
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P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
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P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
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P270	Do not eat, drink or smoke when using this product.
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P281	Use personal protective equipment as required.
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P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
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P305	IF IN EYES:
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P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
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P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
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P370	In case of fire:
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P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
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P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
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P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
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P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
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Disposal
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P501	Dispose of contents/container to ...
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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
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H222	Extremely flammable aerosol
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H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
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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H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
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H310	Fatal in contact with skin
H311	Toxic in contact with skin
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H314	Causes severe skin burns and eye damage
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H318	Causes serious eye damage
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H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
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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

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CAS No.: 13850-91-4

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CAS No.: 13850-91-4

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Product Details of Boc-N-Me-DL-Val-OH

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Application In Synthesis of Boc-N-Me-DL-Val-OH

[ 13850-91-4 ] Synthesis Path-Downstream 1~35

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