Benzyl 2-bromoacetate supplier

Name
Benzyl 2-bromoacetate
EINECS 226-611-4
CAS No. 5437-45-6
Article Data65
CAS DataBase
Density 1.474 g/cm³
Solubility Not miscible or difficult to mix in water.
Melting Point 199-201 °C(Solv: water (7732-18-5))
Formula C₉H₉BrO₂
Boiling Point 287.773 °C at 760 mmHg
Molecular Weight 229.073
Flash Point 116.485 °C
Transport Information UN 2810
Appearance Colorless or light yellow liquid
Safety 26-37/39
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Aceticacid, bromo-, benzyl ester (6CI,7CI,8CI);Acetic acid, bromo-, phenylmethylester (9CI);Benzyl bromoacetate;Bromoacetic acidbenzyl ester;Merbac 35;NSC 16114;NSC 23980;Phenylmethyl bromoacetate;Benzyl 2-bromoacetate;
PSA 26.30000
LogP 2.12470

Synthetic route

: 79-08-3
bromoacetic acid

: 100-51-6
benzyl alcohol

: 5437-45-6
Benzyl bromoacetate

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In benzene at 120℃; for 24h;	100%
With toluene-4-sulfonic acid In benzene at 120℃; for 24h; Inert atmosphere;	100%
With toluene-4-sulfonic acid In benzene at 120℃; for 24h;	100%

: 598-21-0
2-Bromoacetyl bromide

: 100-51-6
benzyl alcohol

: 5437-45-6
Benzyl bromoacetate

Conditions

Conditions	Yield
With sodium hydrogencarbonate In acetonitrile at 0℃; for 0.916667h; Sealed tube; Inert atmosphere;	98%
With dmap In dichloromethane at 20℃; for 2h; Inert atmosphere;	94%
With 2,6-dimethylpyridine In dichloromethane at 0℃; for 2h;	91%

: 96-32-2
bromoacetic acid methyl ester

: 100-51-6
benzyl alcohol

: 5437-45-6
Benzyl bromoacetate

Conditions

Conditions	Yield
With 1,3-bis(2,4,6-trimethylphenyl)imidazole hydrochloride; potassium tert-butylate In benzene at 80℃; for 10h; Inert atmosphere;	85%

: 79-08-3
bromoacetic acid

: 100-51-6
benzyl alcohol

A: 103-50-4
dibenzyl ether

B: 5437-45-6
Benzyl bromoacetate

Conditions

Conditions	Yield
In neat (no solvent) at 80℃; for 6h; Inert atmosphere;	A n/a B 82%

...Expand

: benzyl 2-(tributylstannyl)acetate

: 5437-45-6
Benzyl bromoacetate

Conditions

Conditions	Yield
With tetrabutylammonium hexanitratocerate(IV); carbon tetrabromide; potassium carbonate In acetonitrile at 0℃; for 2h;	68%

: 105-36-2
ethyl bromoacetate

: 100-51-6
benzyl alcohol

: 5437-45-6
Benzyl bromoacetate

Conditions

Conditions	Yield
With toluene-4-sulfonic acid; toluene unter Entfernen des entstehenden Aethanols;

: 13837-45-1
1-ethoxy-1-cyclopropanol

: 78385-35-0
benzyloxycarbonylbromomethylenetriphenylphosphorane

A: 78385-37-2
benzyl 2-bromocyclopropylideneacetate

B: 5437-45-6
Benzyl bromoacetate

Conditions

Conditions	Yield
In benzene for 3.5h; Yields of byproduct given;

...Expand

: 78385-35-0
benzyloxycarbonylbromomethylenetriphenylphosphorane

A: 78385-37-2
benzyl 2-bromocyclopropylideneacetate

B: 5437-45-6
Benzyl bromoacetate

Conditions

Conditions	Yield
With 1-ethoxypropanol; benzoic acid In benzene for 3.5h; Yield given;

: 103-50-4
dibenzyl ether

: 598-21-0
2-Bromoacetyl bromide

A: 100-39-0
benzyl bromide

B: 5437-45-6
Benzyl bromoacetate

Conditions

Conditions	Yield
at 100℃; for 10h; Product distribution;

...Expand

: benzyl bromo acetate

: 108-95-2
phenol

: 5437-45-6
Benzyl bromoacetate

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide

: 79-08-3
bromoacetic acid

: 100-51-6
benzyl alcohol

: 5437-45-6
Benzyl bromoacetate

Conditions

Conditions	Yield
With sulfuric acid; sodium acetate trihydrate; sodium hydrogencarbonate; toluene-4-sulfonic acid; acetic acid; benzyl alcohol; aluminum nickel In ethanol; cyclohexane; water

: 110-86-1
pyridine

: 5437-45-6
Benzyl bromoacetate

: 136383-19-2
N-(Benzyloxycarbonylmethyl)pyridinium bromide

Conditions

Conditions	Yield
	100%
In acetone at 60℃; Inert atmosphere;

: 7662-76-2
tert-butyl 2-(benzylamino)acetate

: 5437-45-6
Benzyl bromoacetate

: 185426-26-0
(Benzyl-benzyloxycarbonylmethyl-amino)-acetic acid tert-butyl ester

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide 1.) 0 deg C, 30 min, 2.) room temperature, 3 h;	100%

: 174799-52-1
tert-butyl {2-[benzylamino]ethyl}carbamate

: 5437-45-6
Benzyl bromoacetate

benzyl 2-(benzyl{2-[(tert-butoxycarbonyl)amino]ethyl}amino)acetate: benzyl 2-(benzyl{2-[(tert-butoxycarbonyl)amino]ethyl}amino)acetate

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide 1.) 0 deg C, 30 min, 2.) room temperature, 3 h;	100%
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0 - 20℃;	90%

: 90914-08-2
N-[N-(tert-Butyloxycarbonyl)-3-aminopropyl]benzylamine

: 5437-45-6
Benzyl bromoacetate

: 174799-95-2
[Benzyl-(3-tert-butoxycarbonylamino-propyl)-amino]-acetic acid benzyl ester

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide 1.) 0 deg C, 30 min, 2.) room temperature, 3 h;	100%

: 90914-09-3
N(1)-benzyl-N(4)-(tert-butyloxycarbonyl)-1,4-diaminobutane

: 5437-45-6
Benzyl bromoacetate

: 174799-96-3
[Benzyl-(4-tert-butoxycarbonylamino-butyl)-amino]-acetic acid benzyl ester

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide 1.) 0 deg C, 30 min, 2.) room temperature, 3 h;	100%

: 174799-53-2
(6-Benzylamino-hexyl)-carbamic acid tert-butyl ester

: 5437-45-6
Benzyl bromoacetate

: 174799-97-4
[Benzyl-(6-tert-butoxycarbonylamino-hexyl)-amino]-acetic acid benzyl ester

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide 1.) 0 deg C, 30 min, 2.) room temperature, 3 h;	100%

: 214412-65-4
(1R,5R)-6-hydroxy-7-oxo-2,6-diazabicyclo[3.2.0]heptane-2-carboxylic acid tert-butyl ester

: 5437-45-6
Benzyl bromoacetate

: 214412-66-5
(1S,5R)-6-Benzyloxycarbonylmethoxy-7-oxo-2,6-diaza-bicyclo[3.2.0]heptane-2-carboxylic acid tert-butyl ester

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 0℃; for 1h;	100%

: (1R,3S)-1-[(1-adamantyl)methyl]-2-acetyl-1-(2-fluorobenzyl)-3-tert-butyloxycarbonylmethylcarbonyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole

: 5437-45-6
Benzyl bromoacetate

: 303767-15-9
2-[2-acetyl-1-adamantan-1-ylmethyl-9-(2-fluoro-benzyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carbonyl]-succinic acid 4-benzyl ester 1-tert-butyl ester

Conditions

Conditions	Yield
Stage #1: (1R,3S)-1-[(1-adamantyl)methyl]-2-acetyl-1-(2-fluorobenzyl)-3-tert-butyloxycarbonylmethylcarbonyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole With sodium hydride In tetrahydrofuran at 0℃; for 0.333333h; Metallation; Stage #2: Benzyl bromoacetate In tetrahydrofuran at 20℃; for 2h; Alkylation; Further stages.;	100%

: 122-52-1
triethyl phosphite

: 5437-45-6
Benzyl bromoacetate

: 7396-44-3
benzyl diethylphosphonoacetate

Conditions

Conditions	Yield
at 150℃;	100%
at 50℃; for 2h;	97%
at 200℃; for 1h;	87%
at 80℃; for 1h;

: 99-93-4
4-Hydroxyacetophenone

: 5437-45-6
Benzyl bromoacetate

: 851875-31-5
benzyl 2-(4-acetylphenoxy)acetate

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1.5h; Williamson ether synthesis;	100%
With potassium carbonate In N,N-dimethyl-formamide at 75 - 80℃; for 1.5h;	79.8%

: 808733-44-0
FmocNHNH(CH2)3NHBoc

: 5437-45-6
Benzyl bromoacetate

: 872554-77-3
Fmoc-aza-β3-Orn(Boc)-Bn

Conditions

Conditions	Yield
With potassium carbonate In toluene for 36h; Reflux;	100%
With potassium carbonate In toluene for 28h; Heating;	60%

: 153086-78-3
tert-butyl {2-[2-(2-aminoethoxy)ethoxy]ethyl}carbamate

: 5437-45-6
Benzyl bromoacetate

: 875057-36-6
(benzyloxycarbonylmethyl-{2-[2-(2-tert-butoxycarbonylamino-ethoxy)-ethoxy]-ethyl}-amino)-acetic acid benzyl ester

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran; water at 20℃; for 12h;	100%

: 31252-42-3
4-benzylpyperidine

: 5437-45-6
Benzyl bromoacetate

: 438634-63-0
(4-benzylpiperidin-1-yl)acetic acid benzyl ester

Conditions

Conditions	Yield
With triethylamine In dichloromethane; ethyl acetate	100%

: 866464-53-1
methyl 2-(m-chlorobenzylideneamino)acetate

: 5437-45-6
Benzyl bromoacetate

: 1175019-83-6
1,3-dibenzyl-2-methyl 2-(3-chlorobenzylideneamino)propane-1,2,3-tricarboxylate

Conditions

Conditions	Yield
Stage #1: methyl 2-(m-chlorobenzylideneamino)acetate With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Stage #2: Benzyl bromoacetate In tetrahydrofuran at -78 - 20℃; Inert atmosphere;	100%

: (2R,3R)-dimethyl 2-(7,8-dihydroxy-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-6-yloxy)-3-(3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-yloxy)succinate

: 5437-45-6
Benzyl bromoacetate

: (2R, 3R)-dimethyl 2-(8-(2-(benzyloxy)-2-oxoethoxy)-7-hydroxy-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-6-yloxy)-3-(3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-yloxy)succinate

Conditions

Conditions	Yield
Stage #1: (2R,3R)-dimethyl 2-(7,8-dihydroxy-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-6-yloxy)-3-(3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-yloxy)succinate With di(n-butyl)tin oxide In methanol for 2h; Inert atmosphere; Reflux; Stage #2: Benzyl bromoacetate With cesium fluoride In tetrahydrofuran for 1.25h; Inert atmosphere;	100%

: 59989-18-3
5-ethynyluracil

: 5437-45-6
Benzyl bromoacetate

: benzyl 2-[4-(uracil-5-yl)-1H-1,2,3-triazol-1-yl]acetate

Conditions

Conditions	Yield
Stage #1: Benzyl bromoacetate With copper(l) iodide; sodium azide; sodium L-ascorbate; N,N`-dimethylethylenediamine In ethanol; water at 100℃; for 1h; Stage #2: 5-ethynyluracil In ethanol; water at 100℃; for 0.5h;	100%

: 33468-67-6
2-methyl-4-(trifluoromethyl)-1H-imidazole

: 5437-45-6
Benzyl bromoacetate

: benzyl 2-[2-methyl-4-(trifluoromethyl)imidazol-1-yl]acetate

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile at 60℃;	100%

: 3-(2,2,2-trifluoroacetamido)-N-(2-(trifluoromethyl)benzyl)benzamide

: 5437-45-6
Benzyl bromoacetate

: benzyl 2-(2,2,2-trifluoro-N-(3-((2-(trifluoromethyl)benzyl)carbamoyl)phenyl)acetamido)acetate

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 0 - 20℃;	100%

: tert-butyl 4-hydroxy-[1,1'-biphenyl]-3-carboxylate

: 5437-45-6
Benzyl bromoacetate

: tert-butyl 4-(2-(benzyloxy)-2-oxoethoxy)-[1,1'-biphenyl]-3-carboxylate

Conditions

Conditions	Yield
Stage #1: tert-butyl 4-hydroxy-[1,1'-biphenyl]-3-carboxylate With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.166667h; Stage #2: Benzyl bromoacetate In N,N-dimethyl-formamide at 45℃; for 2h; Williamson Ether Synthesis;	100%

: 107-96-0
3-mercaptopropionic acid

: 5437-45-6
Benzyl bromoacetate

: C12H14O4S

Conditions

Conditions	Yield
Stage #1: 3-mercaptopropionic acid With triethylamine In dichloromethane at 20℃; for 0.166667h; Stage #2: Benzyl bromoacetate In dichloromethane at -20 - 20℃; for 24h;	100%

: 443-81-2
2-bromo-3-fluorophenol

: 5437-45-6
Benzyl bromoacetate

: benzyl 2-(2-bromo-3-fluorophenoxy)acetate

Conditions

Conditions	Yield
With potassium phosphate In acetonitrile at 20℃; for 16h; Inert atmosphere;	99.5%

: 185426-12-4
6-Benzylamino-hexanoic acid tert-butyl ester

: 5437-45-6
Benzyl bromoacetate

: 185426-28-2
6-(Benzyl-benzyloxycarbonylmethyl-amino)-hexanoic acid tert-butyl ester

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide 1.) 0 deg C, 30 min, 2.) room temperature, 3 h;	99.1%

: 60-34-4
methylhydrazine

: 5437-45-6
Benzyl bromoacetate

: 55501-33-2
benzyl 2-(1-methylhydrazinyl)acetate

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 2h;	99%
With triethylamine In dichloromethane 1.) 0 deg C, 0.5 h, 2.) r.t., 4 h;	98%

: 5437-45-6
Benzyl bromoacetate

: 140-11-4
Benzyl acetate

Conditions

Conditions	Yield
With indium; sodium dodecyl-sulfate at 60℃; for 0.5h;	99%
With borohydride exchange resin; nickel diacetate In methanol for 1h; Ambient temperature;	98%
With DMBI In tetrahydrofuran for 1h; Heating;	94%

: 350697-62-0
2-[6-[bis[(1,1-dimethylethoxy)carbonyl]amino]-1,4-dihydro-4-oxo-2-pyridinyl]-1,3-bis(1,1-dimethylethyl)ester

: 5437-45-6
Benzyl bromoacetate

: 350697-63-1
Benzyl 2-{[2,6-bis(bis(N-tert-butoxycarbonyl)amino)]-4-pyridyloxy} acetate

Conditions

Conditions	Yield
With tetrabutylammomium bromide; potassium carbonate In dimethyl sulfoxide at 20℃; for 18h;	99%

: 111-66-0
oct-1-ene

: 5437-45-6
Benzyl bromoacetate

: benzyl 4-bromodecanoate

Conditions

Conditions	Yield
With air; triethyl borane In ethanol; water at 25℃; for 1.5h;	99%
With air; triethyl borane; 1-ethyl-3-methylimidazolium tetrafluoroborate at 25℃; for 6h;	86%

: 852060-08-3
3-((S)-3,5-Dioxo-1,4-diaza-spiro[5.5]undec-2-yl)-propionic acid methyl ester

: 5437-45-6
Benzyl bromoacetate

: 1054660-71-7
3-((S)-4-Benzyloxycarbonylmethyl-3,5-dioxo-1,4-diaza-spiro[5.5]undec-2-yl)-propionic acid methyl ester

Conditions

Conditions	Yield
With caesium carbonate In acetonitrile at 50℃; for 2h;	99%

: 851577-43-0
5-(((tert-butoxycarbonyl)amino)methyl)-6-isobutyl-2-methyl-4-(4-methylphenyl)nicotinic acid

: 5437-45-6
Benzyl bromoacetate

: 851578-20-6
2-(benzyloxy)-2-oxoethyl 5-{[(tert-butoxycarbonyl)amino]methyl}-6-isobutyl-2-methyl-4-(4-methylphenyl)nicotinate

Conditions

Conditions	Yield
With potassium carbonate In DMF (N,N-dimethyl-formamide) at 20℃; for 0.5h;	99%

: tris(tert-butyl) 2,2',2''-(1,4,7,10-tetraazacyclododecane-1,4,7-triyl)triacetate hydrobromide

: 5437-45-6
Benzyl bromoacetate

: 192635-89-5
phenylmethyl 2-(1,4,7,10-Tetraaza-4,7,10-tris(((tert-butyl)oxycarbonyl)methyl)cyclododecyl)-acetate

Conditions

Conditions	Yield
With sodium hydrogencarbonate In acetonitrile at 100℃; for 30h;	99%
With sodium hydrogencarbonate In acetonitrile at 100℃; for 30h;	91%
With potassium carbonate In acetonitrile for 24h; Reflux; Inert atmosphere;	90%
Stage #1: tris(tert-butyl) 2,2',2''-(1,4,7,10-tetraazacyclododecane-1,4,7-triyl)triacetate hydrobromide With potassium carbonate In acetonitrile for 0.5h; Stage #2: Benzyl bromoacetate In acetonitrile at 50 - 60℃;

Benzyl 2-bromoacetate Specification

The Benzyl 2-bromoacetate, with the CAS registry number 5437-45-6, is also known as Bromoacetic acidbenzyl ester. It belongs to the product categories of Pharmaceutical Intermediates; Building Blocks; C8 to C9; Carbonyl Compounds; Chemical Synthesis; Esters; Organic Building Blocks. Its EINECS number is 226-611-4. This chemical's molecular formula is C₉H₉BrO₂ and molecular weight is 229.07. What's more, its systematic name is Benzyl bromoacetate. This chemical is stable at common pressure and temperature, and it should be sealed and stored in a cool and dry place. Moreover, it should be protected from light.

Physical properties of Benzyl 2-bromoacetate are: (1)ACD/LogP: 2.368; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.37; (4)ACD/LogD (pH 7.4): 2.37; (5)ACD/BCF (pH 5.5): 37.13; (6)ACD/BCF (pH 7.4): 37.13; (7)ACD/KOC (pH 5.5): 462.66; (8)ACD/KOC (pH 7.4): 462.66; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 26.3 Å²; (13)Index of Refraction: 1.556; (14)Molar Refractivity: 49.942 cm³; (15)Molar Volume: 155.421 cm³; (16)Polarizability: 19.798×10^-24cm³; (17)Surface Tension: 44.1 dyne/cm; (18)Density: 1.474 g/cm³; (19)Flash Point: 116.485 °C; (20)Enthalpy of Vaporization: 52.697 kJ/mol; (21)Boiling Point: 287.773 °C at 760 mmHg; (22)Vapour Pressure: 0.002 mmHg at 25°C.

Preparation: this chemical can be prepared by bromoacetic acid and phenylmethanol. This reaction will need reagents DCC, DMAP and solvent tetrahydrofuran with the reaction time of 16 hours. The yield is about 57%.

Benzyl 2-bromoacetate can be prepared by bromoacetic acid and phenylmethanol

Uses of Benzyl 2-bromoacetate: it can be used to produce morpholin-4-yl-acetic acid benzyl ester at the ambient temperature. It will need solvent CH₂Cl₂ with the reaction time of 16 hours. The yield is about 91%.

Benzyl 2-bromoacetate can be used to produce morpholin-4-yl-acetic acid benzyl ester at the ambient temperature

When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. When using it, you need wear suitable protective gloves and eye/face protection.

You can still convert the following datas into molecular structure:
(1)SMILES: BrCC(=O)OCc1ccccc1
(2)Std. InChI: InChI=1S/C9H9BrO2/c10-6-9(11)12-7-8-4-2-1-3-5-8/h1-5H,6-7H2
(3)Std. InChIKey: JHVLLYQQQYIWKX-UHFFFAOYSA-N

Product Name

Benzyl 2-bromoacetate

Synthetic route

Benzyl 2-bromoacetate Specification

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