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117445-22-4

Basic Information
CAS No.: 117445-22-4
Name: Boc-3-Aminomethylbenzoic acid
Article Data: 9
Molecular Structure:
Molecular Structure of 117445-22-4 (Boc-3-Aminomethylbenzoic acid)
Formula: C13H17NO4
Molecular Weight: 251.282
Synonyms: 3-((N-tert-Butoxycarbonylamino)methyl)benzoicacid;3-Boc-aminomethylbenzoic acid;3-[(tert-Butoxycarbonylamino)methyl]benzoicacid;
EINECS: 820-537-1
Density: 1.179 g/cm3
Boiling Point: 434.594 °C at 760 mmHg
Flash Point: 216.635 °C
Appearance: white crystal powder
Safety: 24/25
PSA: 75.63000
LogP: 2.80040
Synthetic route
58632-95-4

2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile

2393-20-6

3-aminomethylbenzoic acid

117445-22-4

3-(tert-butoxycarbonylamino-methyl)benzoic acid

Conditions
ConditionsYield
With triethylamine75%
2393-20-6

3-aminomethylbenzoic acid

117445-22-4

3-(tert-butoxycarbonylamino-methyl)benzoic acid

Conditions
ConditionsYield
With di-tert-butyl dicarbonate; triethylamine In 1,4-dioxane; water68%
58632-95-4

2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile

876-03-9

3-(aminomethyl)benzoic acid hydrochloride

117445-22-4

3-(tert-butoxycarbonylamino-methyl)benzoic acid

Conditions
ConditionsYield
With triethylamine In water Ambient temperature;64%
180863-55-2

methyl 3-(((tert-butoxycarbonyl)amino)methyl)benzoate

117445-22-4

3-(tert-butoxycarbonylamino-methyl)benzoic acid

Conditions
ConditionsYield
Stage #1: methyl 3-(((tert-butoxycarbonyl)amino)methyl)benzoate With water; lithium hydroxide In tetrahydrofuran at 25 - 50℃; for 4h;
Stage #2: With acetic acid In ethyl acetate
44%
Stage #1: methyl 3-(((tert-butoxycarbonyl)amino)methyl)benzoate With water; lithium hydroxide In tetrahydrofuran at 50℃; for 4h;
Stage #2: With acetic acid
44%
24424-99-5

di-tert-butyl dicarbonate

2393-20-6

3-aminomethylbenzoic acid

117445-22-4

3-(tert-butoxycarbonylamino-methyl)benzoic acid

Conditions
ConditionsYield
With sodium hydroxide In 1,4-dioxane
With sodium hydrogencarbonate In 1,4-dioxane; water
1877-72-1

3-Cyanobenzoic acid

117445-22-4

3-(tert-butoxycarbonylamino-methyl)benzoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: NH3 / Raney Ni / ethanol / 51714.8 Torr
2: aq. NaOH / dioxane
View Scheme
Multi-step reaction with 2 steps
1: 64 percent / H2, conc. HCl / 10percent Pd/C / ethanol / 38 h
2: 64 percent / Et3N / H2O / Ambient temperature
View Scheme
Multi-step reaction with 2 steps
1: 95 percent / hydrogen / Pd/C
2: 75 percent / triethylamine
View Scheme
1877-72-1

3-Cyanobenzoic acid

24424-99-5

di-tert-butyl dicarbonate

117445-22-4

3-(tert-butoxycarbonylamino-methyl)benzoic acid

Conditions
ConditionsYield
palladium on carbon In ethanol
75-09-2

dichloromethane

1877-72-1

3-Cyanobenzoic acid

24424-99-5

di-tert-butyl dicarbonate

117445-22-4

3-(tert-butoxycarbonylamino-methyl)benzoic acid

Conditions
ConditionsYield
palladium In methanol; ethanol
6515-58-8

3-bromomethylbenzoic acid

117445-22-4

3-(tert-butoxycarbonylamino-methyl)benzoic acid

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: thionyl chloride / 1 h / 25 °C / Reflux
2: N,N-dimethyl-formamide / 12 h / 85 °C
3: hydrazine hydrate / methanol / 4 h / 25 °C / Reflux
4: sodium hydrogencarbonate / ethyl acetate; water / 1.17 h / pH 8
5: water; lithium hydroxide / tetrahydrofuran / 4 h / 25 - 50 °C
View Scheme
Multi-step reaction with 5 steps
1: thionyl chloride / 1 h / 25 °C / Reflux
2: N,N-dimethyl-formamide / 12 h / 85 °C
3: hydrazine hydrate / methanol / 4 h / Reflux
4: sodium hydrogencarbonate / ethyl acetate; water / 1.17 h / pH 8
5: water; lithium hydroxide / tetrahydrofuran / 4 h / 50 °C
View Scheme
99-04-7

m-Toluic acid

117445-22-4

3-(tert-butoxycarbonylamino-methyl)benzoic acid

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: N-Bromosuccinimide / 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 3 h / 25 °C / Reflux
2: thionyl chloride / 1 h / 25 °C / Reflux
3: N,N-dimethyl-formamide / 12 h / 85 °C
4: hydrazine hydrate / methanol / 4 h / 25 °C / Reflux
5: sodium hydrogencarbonate / ethyl acetate; water / 1.17 h / pH 8
6: water; lithium hydroxide / tetrahydrofuran / 4 h / 25 - 50 °C
View Scheme
Multi-step reaction with 6 steps
1: N-Bromosuccinimide / 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 3 h / 25 °C / Reflux
2: thionyl chloride / 1 h / 25 °C / Reflux
3: N,N-dimethyl-formamide / 12 h / 85 °C
4: hydrazine hydrate / methanol / 4 h / Reflux
5: sodium hydrogencarbonate / ethyl acetate; water / 1.17 h / pH 8
6: water; lithium hydroxide / tetrahydrofuran / 4 h / 50 °C
View Scheme
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  • Boc-3-Aminomethylbenzoic acid  CAS 117445-22-4

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    Boc-3-Aminomethylbenzoic acid CAS 117445-22-4

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Specification

This chemical is called Benzoic acid, 3-[[[(1,1-dimethylethoxy)carbonyl]amino]methyl]-, and its systematic name is 3-{[(tert-butoxycarbonyl)amino]methyl}benzoic acid. With the molecular formula of C13H17NO4, its molecular weight is 251.28. The CAS registry number of this chemical is 117445-22-4. Additionally, its product categories are Pharmacetical; Aromatic Amino Acids; Peptide Synthesis; Unnatural Amino Acid Derivatives.

Other characteristics of the Benzoic acid, 3-[[[(1,1-dimethylethoxy)carbonyl]amino]methyl]- can be summarised as followings: (1)ACD/LogP: 2.57; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.21; (4)ACD/LogD (pH 7.4): -0.33; (5)ACD/BCF (pH 5.5): 2.31; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 26.11; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 5; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 5; (12)Polar Surface Area: 55.84 Å2; (13)Index of Refraction: 1.537; (14)Molar Refractivity: 66.59 cm3; (15)Molar Volume: 213.1 cm3; (16)Polarizability: 26.4×10-24cm3; (17)Surface Tension: 45.2 dyne/cm; (18)Density: 1.178 g/cm3; (19)Flash Point: 216.6 °C; (20)Enthalpy of Vaporization: 72.81 kJ/mol; (21)Boiling Point: 434.6 °C at 760 mmHg; (22)Vapour Pressure: 2.53E-08 mmHg at 25°C.

Production method of this chemical: The Benzoic acid, 3-[[[(1,1-dimethylethoxy)carbonyl]amino]methyl]- could be obtained by the reactants of BOC-on and 3-aminomethyl-benzoic acid. This reaction needs the reagent of triethylamine. The yield is 75 %.

Uses of this chemical: The Benzoic acid, 3-[[[(1,1-dimethylethoxy)carbonyl]amino]methyl]- could react with 4-nitrobenzophenone oxime, and obtain the Boc-Mamb-Ox. This reaction needs the reagent of DCC, DMAP. The yield is 52 %.

You can still convert the following datas into molecular structure: 
1.SMILES: O=C(OC(C)(C)C)NCc1cc(ccc1)C(=O)O
2.InChI: InChI=1/C13H17NO4/c1-13(2,3)18-12(17)14-8-9-5-4-6-10(7-9)11(15)16/h4-7H,8H2,1-3H3,(H,14,17)(H,15,16)
3.InChIKey: MQNHKLMHRZYTBZ-UHFFFAOYAY