Product Name

  • Name

    Isobutyl chloroformate

  • EINECS 208-840-1
  • CAS No. 543-27-1
  • Article Data27
  • CAS DataBase
  • Density 1.081 g/cm3
  • Solubility Insoluble in water and denser than water
  • Melting Point -80 °C
  • Formula C5H9ClO2
  • Boiling Point 130 °C at 760 mmHg
  • Molecular Weight 136.578
  • Flash Point 27.8 °C
  • Transport Information UN 3390 6.1/PG 1
  • Appearance clear liquid
  • Safety 26-36/37/39-45
  • Risk Codes 10-22-23-34
  • Molecular Structure Molecular Structure of 543-27-1 (Isobutyl chloroformate)
  • Hazard Symbols ToxicT
  • Synonyms Formicacid, chloro-, isobutyl ester (6CI,7CI,8CI);2-Methylpropyl carbonochloridate;2-Methylpropyl chloroformate;Chlorocarbonic acid isobutyl ester;Chloroformicacid isobutyl ester;IBCF;Isobutoxycarbonyl chloride;Isobutylcarbonochloridate;Isobutyl chloridocarbonate;Isobutyl chlorocarbonate;Isobutyl chloroformate;Isobutyloxycarbonyl chloride;NSC 8429;Isobutylchloroformate;
  • PSA 26.30000
  • LogP 2.01780

Synthetic route

(R)-N5-[amino-(nitroimino)-methyl]-N2-(diphenylacetyl)ornithine
159013-58-8

(R)-N5-[amino-(nitroimino)-methyl]-N2-(diphenylacetyl)ornithine

N-dimethyl-N'-[4-(aminomethyl) phenyl]urea

N-dimethyl-N'-[4-(aminomethyl) phenyl]urea

A

(R)-N5-[amino(nitroimino)methyl]-N-[[4-[[(dimethylamino)carbonyl]amino]phenyl]methyl]-N2-(diphenylacetyl)-ornithinamide
164645-67-4

(R)-N5-[amino(nitroimino)methyl]-N-[[4-[[(dimethylamino)carbonyl]amino]phenyl]methyl]-N2-(diphenylacetyl)-ornithinamide

B

isobutyl chloroformate
543-27-1

isobutyl chloroformate

Conditions
ConditionsYield
ammoniaA n/a
B 70%
...Expand
phosgene
75-44-5

phosgene

2-methyl-propan-1-ol
78-83-1

2-methyl-propan-1-ol

isobutyl chloroformate
543-27-1

isobutyl chloroformate

Conditions
ConditionsYield
With chloroform
With quinoline; toluene
2-methyl-propan-1-ol
78-83-1

2-methyl-propan-1-ol

bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

isobutyl chloroformate
543-27-1

isobutyl chloroformate

Conditions
ConditionsYield
With sodium carbonate In toluene at 0℃; for 6h;
With pyridine In toluene at 0 - 20℃;
2-methyl-propan-1-ol
78-83-1

2-methyl-propan-1-ol

trichloromethyl chloroformate
503-38-8

trichloromethyl chloroformate

isobutyl chloroformate
543-27-1

isobutyl chloroformate

Conditions
ConditionsYield
With dmap In toluene at 20℃; for 24h;
benzoic acid hydrazide
613-94-5

benzoic acid hydrazide

isobutyl chloroformate
543-27-1

isobutyl chloroformate

N'-Benzoyl-hydrazinecarboxylic acid isobutyl ester
128772-88-3

N'-Benzoyl-hydrazinecarboxylic acid isobutyl ester

Conditions
ConditionsYield
With pyridine In tetrahydrofuran 1) -10 deg C, 30 min, 2) 1 h, room temperature;100%
BOC-glycine
4530-20-5

BOC-glycine

isobutyl chloroformate
543-27-1

isobutyl chloroformate

N-(t-butoxycarbonyl)glycyl i-butyl carbonate
66866-43-1

N-(t-butoxycarbonyl)glycyl i-butyl carbonate

Conditions
ConditionsYield
With 4-methyl-morpholine In tetrahydrofuran at -15℃; for 0.0833333h;100%
With 4-methyl-morpholine In tetrahydrofuran at -20℃; for 0.05h;
(S)-2-tert-butoxycarbonylamino-3-thiophen-2-yl-propionic acid
56675-37-7

(S)-2-tert-butoxycarbonylamino-3-thiophen-2-yl-propionic acid

isobutyl chloroformate
543-27-1

isobutyl chloroformate

C17H25NO6S

C17H25NO6S

Conditions
ConditionsYield
With 4-methyl-morpholine In dichloromethane at -10℃; for 0.05h;100%
N-benzyloxycarbonyl-5-O-benzyl-L-glutamic acid
5680-86-4

N-benzyloxycarbonyl-5-O-benzyl-L-glutamic acid

isobutyl chloroformate
543-27-1

isobutyl chloroformate

(S)-4-Benzyloxycarbonylamino-5-isobutoxycarbonyloxy-5-oxo-pentanoic acid benzyl ester

(S)-4-Benzyloxycarbonylamino-5-isobutoxycarbonyloxy-5-oxo-pentanoic acid benzyl ester

Conditions
ConditionsYield
With 4-methyl-morpholine at -20℃; for 2h;100%
With 4-methyl-morpholine
malonic acid monobenzyl ester
40204-26-0

malonic acid monobenzyl ester

isobutyl chloroformate
543-27-1

isobutyl chloroformate

Malonic acid benzyl ester isobutyl ester
98442-22-9

Malonic acid benzyl ester isobutyl ester

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 4℃; for 0.5h; Mechanism; isotope labelling method;100%
Cbz-Tyr-OH
1164-16-5

Cbz-Tyr-OH

isobutyl chloroformate
543-27-1

isobutyl chloroformate

C22H25NO7
102988-95-4

C22H25NO7

Conditions
ConditionsYield
With 4-methyl-morpholine In tetrahydrofuran at -15℃; for 0.5h;100%
With 4-methyl-morpholine In tetrahydrofuran at -15℃; for 0.0166667h;
With 4-methyl-morpholine In tetrahydrofuran at -15℃; for 0.5h;
3,6-Diisopropyl-2-pyrazinethiol
86799-80-6

3,6-Diisopropyl-2-pyrazinethiol

isobutyl chloroformate
543-27-1

isobutyl chloroformate

isobutyl S-3,6-diisopropylpyrazin-2-ylthiolcarbonate
104272-90-4

isobutyl S-3,6-diisopropylpyrazin-2-ylthiolcarbonate

Conditions
ConditionsYield
With pyridine for 1h; Ambient temperature;100%
(S)-2-(((benzyloxy)carbonyl)amino)-3-(4-hydroxy-3-iodophenyl)propanoic acid
79677-62-6

(S)-2-(((benzyloxy)carbonyl)amino)-3-(4-hydroxy-3-iodophenyl)propanoic acid

isobutyl chloroformate
543-27-1

isobutyl chloroformate

C22H24INO7

C22H24INO7

Conditions
ConditionsYield
With 4-methyl-morpholine In tetrahydrofuran at -15℃; for 0.5h;100%
With 4-methyl-morpholine In tetrahydrofuran at -15℃; for 0.5h;
prostaglandin A2
13345-50-1

prostaglandin A2

isobutyl chloroformate
543-27-1

isobutyl chloroformate

C25H38O6

C25H38O6

Conditions
ConditionsYield
With triethylamine at -20℃; for 0.25h;100%
dinoprost
551-11-1

dinoprost

isobutyl chloroformate
543-27-1

isobutyl chloroformate

C25H42O7

C25H42O7

Conditions
ConditionsYield
With triethylamine at -20℃; for 0.25h;100%
With triethylamine In chloroform at 20℃; for 18h;
11,12-cis-epoxyeicosatrienoic acid
200960-01-6

11,12-cis-epoxyeicosatrienoic acid

isobutyl chloroformate
543-27-1

isobutyl chloroformate

C25H40O5

C25H40O5

Conditions
ConditionsYield
With triethylamine at -20℃; for 0.25h;100%
13-hydroxy-5Z,9Z,11E-octadecatrienoic acid

13-hydroxy-5Z,9Z,11E-octadecatrienoic acid

isobutyl chloroformate
543-27-1

isobutyl chloroformate

C23H38O5

C23H38O5

Conditions
ConditionsYield
With triethylamine at -20℃; for 0.25h;100%
13-oxo-5Z,9Z,11E-octadecatrienoic acid

13-oxo-5Z,9Z,11E-octadecatrienoic acid

isobutyl chloroformate
543-27-1

isobutyl chloroformate

C23H36O5

C23H36O5

Conditions
ConditionsYield
With triethylamine at -20℃; for 0.25h;100%
isobutyl chloroformate
543-27-1

isobutyl chloroformate

isobutyryl chloride
513-36-0

isobutyryl chloride

Conditions
ConditionsYield
With hexabutylguanidinium chloride at 100℃; for 0.666667h;100%
1,3-di-(N-benzylamino)-2-hydroxypropane
65838-17-7

1,3-di-(N-benzylamino)-2-hydroxypropane

isobutyl chloroformate
543-27-1

isobutyl chloroformate

1,3-di-[N-benzyl-N-[(isobutyloxy)carbonyl]amino]-2-hydroxypropane
212912-11-3

1,3-di-[N-benzyl-N-[(isobutyloxy)carbonyl]amino]-2-hydroxypropane

Conditions
ConditionsYield
With triethylamine In dichloromethane100%
With triethylamine In dichloromethane at 0 - 20℃; Carboxylation;98%
malonic acid monobenzyl ester
40204-26-0

malonic acid monobenzyl ester

isobutyl chloroformate
543-27-1

isobutyl chloroformate

A

Malonic acid benzyl ester isobutyl ester
98442-22-9

Malonic acid benzyl ester isobutyl ester

B

CO2

CO2

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 4℃; for 0.5h;A 100%
B n/a
...Expand
methyl (3S)-1,2,3,4-tetrahydro-β-carboline-3-carboxylate
79815-18-2

methyl (3S)-1,2,3,4-tetrahydro-β-carboline-3-carboxylate

isobutyl chloroformate
543-27-1

isobutyl chloroformate

S-methyl 2-i-butoxycarbonyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate

S-methyl 2-i-butoxycarbonyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃;100%
With triethylamine In tetrahydrofuran Heating;67%
(βS,β'S)-dimethylmesobilirubin-XIIIα
144831-30-1

(βS,β'S)-dimethylmesobilirubin-XIIIα

isobutyl chloroformate
543-27-1

isobutyl chloroformate

C45H60N4O10

C45H60N4O10

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran for 1.5h;100%
(1S*,3S*,6R*)-3-methoxy-2-oxabicycl[4.3.0]nonane-1-acetic acid

(1S*,3S*,6R*)-3-methoxy-2-oxabicycl[4.3.0]nonane-1-acetic acid

isobutyl chloroformate
543-27-1

isobutyl chloroformate

(1SR,3SR,6RS)-3-methoxy-2-oxabicyclo[4.3.0]nonan-1-acetic acid O-isobutyrylcarbonic anhydride

(1SR,3SR,6RS)-3-methoxy-2-oxabicyclo[4.3.0]nonan-1-acetic acid O-isobutyrylcarbonic anhydride

Conditions
ConditionsYield
With triethylamine In diethyl ether for 4h;100%
With triethylamine In diethyl ether for 4h;100%
Z-D-proline
6404-31-5

Z-D-proline

isobutyl chloroformate
543-27-1

isobutyl chloroformate

(R)-2-(2-Chloro-acetyl)-pyrrolidine-1-carboxylic acid benzyl ester
741703-34-4

(R)-2-(2-Chloro-acetyl)-pyrrolidine-1-carboxylic acid benzyl ester

Conditions
ConditionsYield
Stage #1: Z-D-proline; isobutyl chloroformate With 4-methyl-morpholine In tetrahydrofuran at -15 - 20℃; for 0.166667h;
Stage #2: With diazomethane; potassium hydroxide; N-Methyl-N'-nitro-N-nitrosoguanidine In diethyl ether; water at 0 - 20℃; for 1h;		100%
2-{3-methyl-2-[(2-phenoxy-ethylcarbamoyl)-methyl]-butyrylamino}-succinic acid 4-tert-butyl ester

2-{3-methyl-2-[(2-phenoxy-ethylcarbamoyl)-methyl]-butyrylamino}-succinic acid 4-tert-butyl ester

isobutyl chloroformate
543-27-1

isobutyl chloroformate

4-amino-3-{3-methyl-2-[(2-phenoxy-ethylcarbamoyl)-methyl]-butyrylamino}-4-oxo-butanoic acid tert-butyl ester

4-amino-3-{3-methyl-2-[(2-phenoxy-ethylcarbamoyl)-methyl]-butyrylamino}-4-oxo-butanoic acid tert-butyl ester

Conditions
ConditionsYield
With 4-methyl-morpholine In dichloromethane at -45℃; for 0.25h;100%
3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carboxylic acid
443956-14-7

3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carboxylic acid

isobutyl chloroformate
543-27-1

isobutyl chloroformate

6-hydroxymethyl-4H-pyrido[3,2-b][1,4]thiazin-3-one
443956-15-8

6-hydroxymethyl-4H-pyrido[3,2-b][1,4]thiazin-3-one

Conditions
ConditionsYield
Stage #1: 3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carboxylic acid; isobutyl chloroformate With triethylamine In tetrahydrofuran at -10 - 0℃; for 0.333333h;
Stage #2: With sodium tetrahydroborate In tetrahydrofuran; water for 0.5h; pH=7;		100%
Stage #1: 3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carboxylic acid; isobutyl chloroformate With triethylamine In tetrahydrofuran at -10℃; for 0.333333h;
Stage #2: With sodium tetrahydroborate In tetrahydrofuran; water for 0.5h;
Stage #3: With hydrogenchloride In tetrahydrofuran; water pH=7;
Z-Leu-OH
2018-66-8

Z-Leu-OH

isobutyl chloroformate
543-27-1

isobutyl chloroformate

N-benzyloxycarbonyl-L-leucinamide
4801-79-0

N-benzyloxycarbonyl-L-leucinamide

Conditions
ConditionsYield
With 4-methyl-morpholine; ammonia In tetrahydrofuran; ethyl acetate100%
With 4-methyl-morpholine; ammonia In tetrahydrofuran; ethyl acetate100%
With 4-methyl-morpholine; ammonia In tetrahydrofuran; ethyl acetate100%
With 4-methyl-morpholine; ammonia In methanol; dichloromethane
ammonium hydroxide
1336-21-6

ammonium hydroxide

cis-[4-cyano-4-(3-cyclopropylmethoxy-4-methoxyphenyl)-1-methoxycyclohexane-1-carboxylic acid]

cis-[4-cyano-4-(3-cyclopropylmethoxy-4-methoxyphenyl)-1-methoxycyclohexane-1-carboxylic acid]

isobutyl chloroformate
543-27-1

isobutyl chloroformate

Cis-[4-Cyano-4-(3-Cyclopropylmethoxy-4-Methoxyphenyl)-1-Methoxycyclohexane-1-Carboxamide]

Cis-[4-Cyano-4-(3-Cyclopropylmethoxy-4-Methoxyphenyl)-1-Methoxycyclohexane-1-Carboxamide]

Conditions
ConditionsYield
With 4-methyl-morpholine In 1,2-dimethoxyethane; water100%
...Expand
ethyl acetate-chloroform

ethyl acetate-chloroform

5-fluoro-α-methyltryptamine
61-53-0

5-fluoro-α-methyltryptamine

N-(Benzyloxycarbonyl)glycine
1138-80-3

N-(Benzyloxycarbonyl)glycine

isobutyl chloroformate
543-27-1

isobutyl chloroformate

N-ethyl-N-(N-benzyloxycarbonylglycyl)-tryptamine
79940-68-4

N-ethyl-N-(N-benzyloxycarbonylglycyl)-tryptamine

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran100%
...Expand
Boc-Orn(Z)-OH
2480-93-5

Boc-Orn(Z)-OH

isobutyl chloroformate
543-27-1

isobutyl chloroformate

[4(S)-(+)-tert-butoxycarbonylamino-4-carbamoylbutyl]carbamic acid benzyl ester
130370-47-7

[4(S)-(+)-tert-butoxycarbonylamino-4-carbamoylbutyl]carbamic acid benzyl ester

Conditions
ConditionsYield
Stage #1: Boc-Orn(Z)-OH; isobutyl chloroformate With 4-methyl-morpholine In tetrahydrofuran at -20℃; for 0.25h;
Stage #2: With ammonia In tetrahydrofuran; water at -20 - 0℃; for 3h;		100%
1,1-cyclopropanedicarboxylic acid monomethyl ester
113020-21-6

1,1-cyclopropanedicarboxylic acid monomethyl ester

isobutyl chloroformate
543-27-1

isobutyl chloroformate

methyl 1-(hydroxymethyl)cyclopropane-1-carboxylate
88157-42-0

methyl 1-(hydroxymethyl)cyclopropane-1-carboxylate

Conditions
ConditionsYield
Stage #1: 1,1-cyclopropanedicarboxylic acid monomethyl ester; isobutyl chloroformate With triethylamine In tetrahydrofuran at -10℃; for 1h; Inert atmosphere;
Stage #2: With sodium tetrahydroborate; water In tetrahydrofuran at 0℃; for 2.5h;		100%
With sodium borohydrid; sodium chloride; triethylamine; citric acid In tetrahydrofuran; tetrahydrofuran (100 ml)-water
2-methyl-3-buten-2-ol
115-18-4

2-methyl-3-buten-2-ol

isobutyl chloroformate
543-27-1

isobutyl chloroformate

1,1-dimethylpropenyl isobutyl carbonate

1,1-dimethylpropenyl isobutyl carbonate

Conditions
ConditionsYield
Stage #1: 2-methyl-3-buten-2-ol With n-butyllithium In tetrahydrofuran; hexane at 0℃; Inert atmosphere;
Stage #2: isobutyl chloroformate In tetrahydrofuran; hexane at 0 - 20℃;		100%
4-oxo-cyclohexane-1,3-dicarboxylic acid dimethyl ester
103505-09-5

4-oxo-cyclohexane-1,3-dicarboxylic acid dimethyl ester

isobutyl chloroformate
543-27-1

isobutyl chloroformate

dimethyl 4-(Isobutoxycarbonyloxy)cyclohex-3-ene-1,3-dicarboxylate
1422158-26-6

dimethyl 4-(Isobutoxycarbonyloxy)cyclohex-3-ene-1,3-dicarboxylate

Conditions
ConditionsYield
With triethylamine In toluene at 20℃; for 3h;100%
imino(phenyl)(trifluoromethyl)-λ6-sulfanone
95414-68-9

imino(phenyl)(trifluoromethyl)-λ6-sulfanone

isobutyl chloroformate
543-27-1

isobutyl chloroformate

O-iso-butyl N-[oxo-phenyl(trifluoromethyl)-λ6-sulfanylidene]carbamoate
1448157-70-7

O-iso-butyl N-[oxo-phenyl(trifluoromethyl)-λ6-sulfanylidene]carbamoate

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 0 - 20℃; for 5h; Inert atmosphere;100%

Isobutyl chloroformate Specification

The CAS register number of Carbonochloridicacid, 2-methylpropyl ester is 543-27-1. It also can be called as Isobutyl chloroformate and the IUPAC name about this chemical is 2-methylpropyl carbonochloridate. The molecular formula about this chemical is C5H9ClO2 and the molecular weight is 136.58. It belongs to the following product categories, such as Organics; Chloroformates; Acid Halides; Carbonyl Compounds; Organic Building Blocks and so on.

Physical properties about Carbonochloridicacid, 2-methylpropyl ester are: (1)ACD/LogP: 2.32; (2)ACD/LogD (pH 5.5): 2.32; (3)ACD/LogD (pH 7.4): 2.32; (4)ACD/BCF (pH 5.5): 34.08; (5)ACD/BCF (pH 7.4): 34.08; (6)ACD/KOC (pH 5.5): 435.07; (7)ACD/KOC (pH 7.4): 435.07; (8)#H bond acceptors: 2; (9)#Freely Rotating Bonds: 3; (10)Polar Surface Area: 26.3Å2; (11)Index of Refraction: 1.417; (12)Molar Refractivity: 31.79 cm3; (13)Molar Volume: 126.3 cm3; (14)Polarizability: 12.6x10-24cm3; (15)Surface Tension: 28.4 dyne/cm; (16)Enthalpy of Vaporization: 36.77 kJ/mol; (17)Boiling Point: 130 °C at 760 mmHg; (18)Vapour Pressure: 9.91 mmHg at 25°C.

Uses of Carbonochloridicacid, 2-methylpropyl ester: it can be used to produce phenethyl-carbamic acid isobutyl ester with phenethylamine at ambient temperature. This reaction will need reagent pyridine and solvent CH2Cl2 with reaction time of 3 hours.

When you are using this chemical, please be cautious about it as the following:
This chemical is toxic by inhalation and it is harmful if swallowed, it is flammable and it can cause burns. When you are using it, wear suitable protective clothing, gloves and eye/face protection. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice and in case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)

You can still convert the following datas into molecular structure:
(1)SMILES: ClC(=O)OCC(C)C
(2)InChI: InChI=1/C5H9ClO2/c1-4(2)3-8-5(6)7/h4H,3H2,1-2H3
(3)InChIKey: YOETUEMZNOLGDB-UHFFFAOYAL
(4)Std. InChI: InChI=1S/C5H9ClO2/c1-4(2)3-8-5(6)7/h4H,3H2,1-2H3
(5)Std. InChIKey: YOETUEMZNOLGDB-UHFFFAOYSA-N

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