4048-33-3

Basic information

• Product Name: 6-Amino-1-hexanol
• Synonyms: 6-Aminohexan-1-ol;6-Hydroxy-1-hexylamine;6-Amino-1-hexanol,97%;6-Hexanolamine;6-Aminohexane-1-ol;Hexanolamine;6-Amino-1-hexanol,94%;6-Amino-1-hexanol ,98%
• CAS NO: 4048-33-3
• Molecular Formula: C₆H₁₅NO
• Molecular Weight: 117.19
• EINECS: 223-748-1
• Product Categories: omega-Aminoalkanols;omega-Functional Alkanols, Carboxylic Acids, Amines & Halides;Amino Alcohols;Organic Building Blocks;Oxygen Compounds
• Mol File: 4048-33-3.mol
• Article Data: 29

Chemical Properties

• Melting Point: 54-58 °C(lit.)
• Boiling Point: 135-140 °C30 mm Hg(lit.)
• Flash Point: 133 °C
• Appearance: Light yellow to brown/Crystals
• Density: 0.8872 (estimate)
• Vapor Pressure: 0.0156mmHg at 25°C
• Refractive Index: 1.4444 (estimate)
• Storage Temp.: Store at?0-5°C
• Solubility: DMSO (Slightly), Chloroform (Slightly), Methanol (Slightly)
• PKA: 15.18±0.10(Predicted)
• Water Solubility: MISCIBLE
• Sensitive: Hygroscopic
• Stability: Hygroscopic. Stable. Incompatible with strong oxidizing agents.
• BRN: 1732524
• CAS DataBase Reference: 6-Amino-1-hexanol(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Amino-1-hexanol(4048-33-3)
• EPA Substance Registry System: 6-Amino-1-hexanol(4048-33-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-36
• WGK Germany: 3
• RTECS: MO8840000
• F: 3-10
• HazardClass: IRRITANT, HYGROSCOPIC
• Hazardous Substances Data: 4048-33-3(Hazardous Substances Data)

Usage

Chemical Properties

slightly yellow crystalline powder

Uses

Different sources of media describe the Uses of 4048-33-3 differently. You can refer to the following data:
1. 6-Amino-1-hexanol is used in the synthesis of guanidino analogs of roscovitine, which is a cyclin-dependant kinase. Also used in the preparation of tocotrienols which maintain anticancer, antiprolifer ative and antimigratory activity. Behery, F
2. 6-Amino-1-hexanol is used as pharmaceutical intermediate.
3. 6-Amino-1-hexanol can undergo cyclization over copper supported on γ-alumina and magnesia to form hexahydro-1H-azepine. It may be used along with glutaric acid to generate poly(ester amide)s with excellent film- and fiber forming properties.

InChI:InChI=1/C6H15NO/c7-5-3-1-2-4-6-8/h8H,1-7H2/p+1

Synthetic route

6-aminohexanoic acid (60-32-2) → 6-amino-1-hexanol (4048-33-3)

Conditions	Yield
Stage #1: 6-aminohexanoic acid With sodium tetrahydroborate at 40℃; for 0.333333h; Sonication; Stage #2: In ethylene glycol at 90℃; for 16.5h; Reflux; Stage #3: With water In ethylene glycol Temperature;	96%
With sodium tetrahydroborate; iodine In tetrahydrofuran

N-benzyloxycarbonyl-6-amino-1-hexanol (17996-12-2) → 6-amino-1-hexanol (4048-33-3)

Conditions	Yield
With lithium borohydride; chloro-trimethyl-silane In tetrahydrofuran for 24h; Ambient temperature;	95%
With hydrogen bromide for 4h;	79%

caprolactam (105-60-2) → 6-amino-1-hexanol (4048-33-3)

Conditions	Yield
Stage #1: caprolactam With sodium hydroxide In toluene at 80℃; Stage #2: In toluene at 100℃; for 16h; Stage #3: With ammonium chloride for 0.25h; Temperature;	87.2%
With [RuCl2(Ph2PCH2CH2NH2)2]; potassium tert-butylate; hydrogen; zinc(II) trifluoroacetate In 1,4-dioxane at 100℃; under 22502.3 Torr; for 18h; Inert atmosphere; Autoclave;	77%
With ethanol; sodium

N-CO2CH3-6-amino-1-hexanol (163361-15-7) → 6-amino-1-hexanol (4048-33-3)

Conditions	Yield
With hydrogenchloride In water for 3h; Reflux;	85%

1,6-Hexanediamine (124-09-4) → hexamethylene imine (111-49-9) + 6-amino-1-hexanol (4048-33-3)

Conditions	Yield
With carbonylchloro[4,5-bis(diisopropylphosphinomethyl)acridine]hydridoruthenium(II) In 1,4-dioxane; water at 100℃; for 40h; Schlenk technique; Inert atmosphere;	A 70% B 10%

6-(Boc-amino)-1-hexanol (75937-12-1) → 6-amino-1-hexanol (4048-33-3)

Conditions	Yield
With trifluoroacetic acid at 20℃; for 12h;	65%

6-azidohexan-1-ol (146292-90-2) → 6-amino-1-hexanol (4048-33-3)

Conditions	Yield
With aluminum oxide; potassium hydroxide; hydrazine In neat (no solvent) for 1h; Milling;	60%

1,6-hexanediol (629-11-8) → hexamethylene imine (111-49-9) + 1,6-Hexanediamine (124-09-4) + 6-amino-1-hexanol (4048-33-3)

Conditions	Yield
With ammonia; hydrogen In water at 180℃; under 7500.75 - 27752.8 Torr; for 4h; Reagent/catalyst; Solvent; Pressure; Time;	A 19.5% B 23.4% C 17%
With ammonia; chlorocarbonylhydrido[4,5-bis(dicyclohexylphosphinomethyl)acridine]ruthenium(II) In toluene at 155℃; under 25502.6 Torr; for 12h; Autoclave; Inert atmosphere;
With ammonia; hydrogen In tert-butyl alcohol at 220℃; under 120012 Torr; for 6h; Kinetics; Reagent/catalyst;	A 66.5 %Chromat. B 21.2 %Chromat. C 6.5 %Chromat.
With ammonia; hydrogen In tert-butyl alcohol at 220℃; under 120012 Torr; for 6h; Kinetics; Reagent/catalyst;	A 7.5 %Chromat. B 17.6 %Chromat. C 68.8 %Chromat.
With ammonia; hydrogen In tert-butyl alcohol at 220℃; under 120012 Torr; for 6h; Kinetics;	A 23 %Chromat. B 31.3 %Chromat. C 19.1 %Chromat.

hexamethylene imine (111-49-9) → 6-amino-1-hexanol (4048-33-3)

Conditions	Yield
With water; cobalt at 210℃;
With water at 280℃;

ethyl 6-aminohexanoate (371-34-6) → 6-amino-1-hexanol (4048-33-3)

Conditions	Yield
With lithium aluminium tetrahydride; diethyl ether

6-acetoxy-hexanenitrile (34957-71-6) → 6-amino-1-hexanol (4048-33-3)

Conditions	Yield
With ammonia; nickel at 140℃; under 95616 Torr; Hydrogenation.beim Erhitzen des Reaktionsprodukts mit wss. Natronlauge;

6-acetoxy-hexanenitrile (34957-71-6) → 6-amino-1-hexanol (4048-33-3) + acetic acid-(6-amino-hexyl ester) (98487-02-6)

Conditions	Yield
With ammonia; nickel at 140℃; under 95616 Torr;

1,6-Hexanediamine (124-09-4) → hexamethylene imine (111-49-9) + 6-amino-1-hexanol (4048-33-3) + 2-Methylpiperidin (109-05-7, 3000-79-1)

Conditions	Yield
With water at 300℃; for 15h; Rate constant;	A 37 % Chromat. B n/a C 2 % Chromat.

(+-)-tetrahydro<2>furyl-acetonitrile → 2-(tetrahydrofuran-2-yl)ethylamine (98277-97-5) + 6-amino-1-hexanol (4048-33-3)

Conditions	Yield
With sodium hydroxide; ethanol; nickel under 88260.9 Torr; Hydrogenation;

oxalate of β--ethylamine → 6-amino-1-hexanol (4048-33-3)

Conditions	Yield
With platinum under 1140 - 1520 Torr; Hydrogenation;

1-hydroxy-6-((4-methoxyphenyl)-diphenylmethylamino)-hexane (114729-83-8) → 6-amino-1-hexanol (4048-33-3)

Conditions	Yield
With sodium periodate In acetone at 20℃; for 16h;

5-chloropentyl acetate (20395-28-2) → 6-amino-1-hexanol (4048-33-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium iodide; acetone / beim Erwaermen des Reaktionsprodukts mit Kaliumcyanid in wss. Aethanol 2: Raney nickel; ammonia / 140 °C / 95616 Torr / Hydrogenation.beim Erhitzen des Reaktionsprodukts mit wss. Natronlauge View Scheme
Multi-step reaction with 2 steps 1: sodium iodide; acetone / beim Erwaermen des Reaktionsprodukts mit Kaliumcyanid in wss. Aethanol 2: Raney nickel; ammonia / 140 °C / 95616 Torr View Scheme

4-((6-hydroxyhexylcarbamoyloxy)methyl)-1-methylpyridinium trifluoromethanesulfonate (1345959-35-4) → 6-amino-1-hexanol (4048-33-3) + 1,4-dimethylpyridin-1-ium trifluoromethanesulfonate

Conditions	Yield
With tris(2,2'-bipyridyl)ruthenium dichloride; ascorbic acid In d(4)-methanol for 4h; Photolysis; Inert atmosphere;	A 98 %Spectr. B n/a

1,6-hexanediol (629-11-8) → 1,6-Hexanediamine (124-09-4) + 6-amino-1-hexanol (4048-33-3)

Conditions	Yield
With ammonia; (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II); 1,1,1-tris(diethylphosphinomethyl)ethane In toluene at 155℃; under 31503.2 Torr; for 12h; Product distribution / selectivity; Autoclave;
With ammonia; (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II); bis(2-diphenylphosphinoethyl)phenylphosphine In toluene at 155℃; under 30003 Torr; for 12h; Product distribution / selectivity; Inert atmosphere;
With (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II); ammonia; [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] In toluene at 155℃; under 31503.2 Torr; for 12h; Inert atmosphere; Autoclave;
With (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II); ammonia; [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] In toluene at 155℃; under 31503.2 Torr; for 12h; Pressure; Reagent/catalyst; Autoclave; Inert atmosphere;

1,6-hexanediol (629-11-8) → 6-amino-1-hexanol (4048-33-3)

Conditions	Yield
With ammonia; (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In toluene at 155℃; under 27002.7 Torr; for 12h; Product distribution / selectivity; Inert atmosphere;
With (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II); ammonia; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In toluene at 155℃; under 27002.7 Torr; for 12h; Inert atmosphere; Autoclave;
With (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II); ammonia; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In toluene at 155℃; under 27002.7 Torr; for 12h; Pressure; Reagent/catalyst; Autoclave; Inert atmosphere;

N-methyl N'-(6'-hydroxyhexyl)phthalicdiamide (1445745-29-8) + methylamine (74-89-5) → 6-amino-1-hexanol (4048-33-3) + N1,N2-dimethylphthalamide (19532-98-0)

Conditions	Yield
In water at 20℃; for 0.166667h; Temperature; Reagent/catalyst;

C13H20BNO3 → 6-amino-1-hexanol (4048-33-3) + 2-formylbenzene boronic acid (40138-16-7)

Conditions	Yield
With tris(2-carboxyethyl)phosphine; water In aq. phosphate buffer; water-d2 for 0.0833333h;

5-hydroxymethylfuran-2-ylmethylamine (88910-22-9) → 6-amino-1-hexanol (4048-33-3)

Conditions	Yield
With hydrogen In tetrahydrofuran at 30℃; under 2250.23 Torr; for 72h;

5-hydroxymethyltetrahydrofurfurylamine → 6-amino-1-hexanol (4048-33-3)

Conditions	Yield
With rhenium on alumina; hydrogen In dichloromethane at 90℃; under 13501.4 Torr; for 12h;

n-Pent-4-enyl alcohol (821-09-0) + carbon monoxide (201230-82-2) + benzylamine (100-46-9) → 6-amino-1-hexanol (4048-33-3) + 7-azatridecane-1,13-diol (85652-29-5)

Conditions	Yield
Stage #1: n-Pent-4-enyl alcohol; carbon monoxide; benzylamine With C20H22N2ORh(1+)*C24H20B(1-); hydrogen In toluene at 85℃; under 37503.8 Torr; for 6h; Stage #2: With palladium 10% on activated carbon; hydrogen In ethanol at 75℃; under 3750.38 Torr; for 24h;

6-amino-1-hexanol (4048-33-3) + di-tert-butyl dicarbonate (24424-99-5) → 6-(Boc-amino)-1-hexanol (75937-12-1)

Conditions	Yield
In dichloromethane for 12h;	100%
With triethylamine In tetrahydrofuran	100%
In dichloromethane at 0 - 20℃; for 15h;	100%

6-amino-1-hexanol (4048-33-3) + N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) → (9H-fluoren-9-yl)methyl (6-hydroxyhexyl)carbamate (127903-20-2)

Conditions	Yield
With pyridine In methanol at 23℃; for 16h;	100%
With pyridine In methanol at 23℃;
With sodium carbonate In 1,4-dioxane; water at 20℃; for 0.5h;	11 g

1-benzyl-4-hydroxypiperidine (4727-72-4) + 6-amino-1-hexanol (4048-33-3) → N-(6-Hydroxyhexyl)carbamic acid (1-benzyl-4-piperidinyl) ester

Conditions	Yield
With triethylamine; 1,1'-carbonyldiimidazole In tetrahydrofuran	100%

6-amino-1-hexanol (4048-33-3) + formic acid ethyl ester (109-94-4) → N-(6-hydroxyhexyl)formamide (77525-25-8)

Conditions	Yield
Reflux;	100%
for 20h; Reflux;	27%

6-amino-1-hexanol (4048-33-3) + acetonitrile (75-05-8) → 6-(N,N-diethylamino)-hexanol (6947-12-2)

Conditions	Yield
With palladium 10% on activated carbon; ammonium acetate; hydrogen In methanol at 20℃; under 760.051 Torr; for 34h;	100%

6-amino-1-hexanol (4048-33-3) → 6-bromo-1-aminohexane hydrobromide (14502-76-2)

Conditions	Yield
With hydrogen bromide In water for 3h; Inert atmosphere; Reflux;	100%
With hydrogen bromide In water at 0 - 100℃; for 24h;	94%
With hydrogen bromide at 0 - 80℃; for 20h;	61%
With hydrogen bromide In water for 20h; Reflux;
With hydrogen bromide at 0 - 80℃; for 20h;

6,9-dichloro-1,2,3,4-tetrahydroacridine (5396-25-8) + 6-amino-1-hexanol (4048-33-3) → 6-((6-chloro-1,2,3,4-tetrahydroacridin-9-yl)amino)hexan-1-ol (1440519-90-3)

Conditions	Yield
Stage #1: 6,9-dichloro-1,2,3,4-tetrahydroacridine In phenol at 105℃; for 0.5h; Stage #2: 6-amino-1-hexanol In phenol at 105℃; for 20h;	100%
In pentan-1-ol for 48h; Reflux;	52%

(R)-8-(benzyloxy)-5-(2-bromo-1-((tert-butyldimethylsilyl)oxy)ethyl)quinolin-2(1H)-one (530084-74-3) + 6-amino-1-hexanol (4048-33-3) → (R)-8-(benzyloxy)-5-(1-((tert-butyldimethylsilyl)oxy)-2-((6-hydroxyhexyl)amino)ethyl)quinolin-2-(1H)-one

Conditions	Yield
In 1-methyl-pyrrolidin-2-one at 80℃; for 18h;	100%
In 1-methyl-pyrrolidin-2-one at 80℃; for 18h;	100%

6-amino-1-hexanol (4048-33-3) + tert-butyldimethylsilyl chloride (18162-48-6) → 6-((tert-butyldimethylsilyl)oxy)hexan-1-amine (124883-99-4)

Conditions	Yield
With dmap; triethylamine In dichloromethane at 0 - 20℃; for 18h;	99.3%
With dmap In dichloromethane at 20℃; for 15h;	95%
In pyridine	86%
With 1H-imidazole In N,N-dimethyl-formamide Ambient temperature;	11.2 g

6-amino-1-hexanol (4048-33-3) + 4-tolyl iodide (624-31-7) → 6-(p-tolylamino)hexan-1-ol

Conditions	Yield
With 2-(2-methyl-1-oxopropane)cyclohexanone; caesium carbonate; copper(l) iodide In N,N-dimethyl-formamide at 20℃; for 19h;	99%

6-amino-1-hexanol (4048-33-3) + acetonitrile (75-05-8) → N-ethyl-6-hydroxyhexylamine (42055-20-9)

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; under 760.051 Torr; for 46h;	99%

6-amino-1-hexanol (4048-33-3) + 2-adamantanecarbonyl chloride (40079-92-3) → N-(6-hydroxyhexyl)-1-adamantanecarboxamide

Conditions	Yield
With triethylamine In dichloromethane at 20℃;	99%

6-amino-1-hexanol (4048-33-3) + 2,2,2-trifluoroethyl benzoate (1579-72-2) → 6-aminohexyl benzoate (1012797-89-5)

Conditions	Yield
With FeIII-salen In toluene at 120℃; for 2h;	99%
With [1,3-bis(2,4,6-trimethylphenyl)imidazol]-2-ylidene In tetrahydrofuran at 20℃; for 24h; Reagent/catalyst; chemoselective reaction;	91%

6-amino-1-hexanol (4048-33-3) + (R)-Mandelic Acid (611-71-2) → 2-hydroxy-N-(6-hydroxyhexyl)-2-phenylacetamide

Conditions	Yield
With dihydroxy-methyl-borane; water In o-xylene for 12h; Molecular sieve; Reflux; chemoselective reaction;	99%

6-amino-1-hexanol (4048-33-3) + di-tert-butyl dicarbonate (24424-99-5) + 2,2,2-trifluoroethyl benzoate (1579-72-2) → 6-((tert-butoxycarbonyl)amino)hexyl benzoate (1012798-18-3)

Conditions	Yield
Stage #1: 6-amino-1-hexanol; 2,2,2-trifluoroethyl benzoate With (μ-oxo)bis[(1,2-ethanediamino-N,N'-bis(salicylidene))iron(III)] In toluene at 120℃; for 2h; Inert atmosphere; Schlenk technique; Stage #2: di-tert-butyl dicarbonate With triethylamine In dichloromethane at 4 - 20℃; for 4h; Inert atmosphere; Schlenk technique; chemoselective reaction;	99%

6-amino-1-hexanol (4048-33-3) + 5-(6)-carboxytetramethylrhodamine succinimidyl ester → C31H36N3O5(1+)

Conditions	Yield
With sodium hydrogencarbonate In water; dimethyl sulfoxide Cooling with ice;	99%

6-amino-1-hexanol (4048-33-3) + dioleoylphosphatidylcholine (4235-95-4) → (Z)-Octadec-9-enoic acid (R)-2-[(6-amino-hexyloxy)-hydroxy-phosphoryloxy]-1-((Z)-octadec-9-enoyloxymethyl)-ethyl ester

Conditions	Yield
With CaCl2 buffer; sodium acetate; acetic acid In chloroform at 30℃; for 4h; phospholipase D from Streptomyces sp., pH 6.5;	98%

6-amino-1-hexanol (4048-33-3) + (fluorenylmethoxy)carbonyl chloride (28920-43-6) → (9H-fluoren-9-yl)methyl (6-hydroxyhexyl)carbamate (127903-20-2)

Conditions	Yield
With sodium carbonate In 1,4-dioxane at 0 - 25℃; for 12h;	98%
With sodium carbonate In 1,4-dioxane; water at 0 - 20℃; for 1h;	97%
With sodium hydrogencarbonate In 1,4-dioxane at 0 - 20℃;	95%

6-amino-1-hexanol (4048-33-3) + tert-butylchlorodiphenylsilane (58479-61-1) → 1-O-(tert-butyldiphenylsilanyl)-6-hexylamine (216014-70-9)

Conditions	Yield
In pyridine for 16h;	98%
With 1-methyl-1H-imidazole; iodine In dichloromethane at 20℃; for 0.0833333h;	93%
With 1-methyl-1H-imidazole; iodine In dichloromethane at 20℃; for 0.0833333h;	93%
With pyridine

6-amino-1-hexanol (4048-33-3) + trifluoroacetic anhydride (407-25-0) → 6-trifluoroacetamido-1-hexanol (40248-34-8)

Conditions	Yield
With triethylamine In methanol for 16h;	98%
With triethylamine In methanol at 0 - 20℃; Inert atmosphere;	92%
With triethylamine In dichloromethane at 20℃; for 12h; Inert atmosphere; Cooling with ice;

6-amino-1-hexanol (4048-33-3) + 3',6'-bis(cyclohexylcarbonyloxy)-4',5'-dichloro-2',7'-dimethoxy-3-oxospiro[isobenzofuran-1(3H),9'-[9H]xanthene]-5-carboxylic acid pentafluorophenyl ester (1353002-80-8) → 3',6'-bis(cyclohexylcarbonyloxy)-4',5'-dichloro-2',7'-dimethoxy-5-(6-hydroxyhexylaminocarbonyl)-3-oxospiro[isobenzofuran-1(3H),9'-[9H]xanthene] (1353002-84-2)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 2h;	98%

6-amino-1-hexanol (4048-33-3) + perylene-3,4,9,10-tetracarboxylic acid 3,4:9,10-dianhydride (128-69-8) → N,N'-bis(6-hydroxyhexyl)perylene-3,4:9,10-bis(dicarboximide) (107356-24-1)

Conditions	Yield
With 1H-imidazole at 150℃; for 36h;	98%
With zinc acetate dehydrate In N,N-dimethyl acetamide at 110 - 160℃; for 18h; Inert atmosphere;	86%
In ethylene glycol at 140℃; for 16h; Inert atmosphere;	76%

6-amino-1-hexanol (4048-33-3) + benzoyl chloride (98-88-4) → N-(6-hydroxyhexyl)benzamide (97798-40-8)

Conditions	Yield
With sodium hydroxide In dichloromethane; water at 20℃; for 1h; Inert atmosphere;	98%

6-amino-1-hexanol (4048-33-3) + 2-Isocyanatoethyl methacrylate (30674-80-7) → 2-[(6-hydroxyhexylamino)carbonylamino]ethylmethacrylate

Conditions	Yield
In dichloromethane at 0 - 20℃; for 2.25h;	98%

6-amino-1-hexanol (4048-33-3) + N-(1-hexylheptyl)-perylene-3,4,9,10-tetracarboxylic-3,4-carboximide-9,10-anhydride (130296-37-6) → 2-(6-hydroxyhexyl)-9-(tridecan-7-yl)anthra[2,1,9-def:6,5,10-d'e'f']diisoquinoline-1,3,8,10(2H,9H)-tetraone

Conditions	Yield
With 1H-imidazole at 180℃; for 5h;	98%
With 1H-imidazole at 150℃; for 6h;
With 1H-imidazole; N,N-dimethyl acetamide; zinc diacetate
With 1H-imidazole; zinc diacetate; p-dimethylaminocinnamaldehyde
With 1H-imidazole; N,N-dimethyl acetamide; zinc diacetate

6-amino-1-hexanol (4048-33-3) + 3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride (129-64-6) → (3aR,4S,7R,7aS)-2-(6-hydroxyhexyl)-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3(2H)-dione

Conditions	Yield
In toluene for 6h; Reflux; Dean-Stark;	98%

phthalic anhydride (85-44-9) + 6-amino-1-hexanol (4048-33-3) → 6-phthalimido-1-hexanol (63945-11-9)

Conditions	Yield
for 0.0333333h; Condensation; Irradiation;	97%
In toluene Reflux;	96%
at 160℃; for 0.0833333h; Microwave irradiation;	94%

6-amino-1-hexanol (4048-33-3) + 2,4-Dinitrofluorobenzene (70-34-8) → 6-(2,4-dinitrophenylamino)hexan-1-ol (74658-87-0)

Conditions	Yield
With triethylamine In 1,4-dioxane at 20℃; for 1h;	97%
In methanol for 12h;	54%

6-amino-1-hexanol (4048-33-3) + 5-(dimethylamino)naphth-1-ylsulfonyl chloride (605-65-2) → 5-(dimethylamino)-N-(6-hydroxyhexyl)-1-naphthalenesulfonamide (110232-19-4)

Conditions	Yield
With sodium carbonate In tetrahydrofuran; water at 20℃; for 0.5h;	97%
With triethylamine In dichloromethane; N,N-dimethyl-formamide at 20℃; for 7h;	94%
With triethylamine In dichloromethane at 20℃; for 16h; Darkness;	68.5%
With triethylamine In dichloromethane at 20℃;

6-amino-1-hexanol (4048-33-3) → 6-azidohexan-1-ol (146292-90-2)

Conditions	Yield
With copper(ll) sulfate pentahydrate; sodium hydrogencarbonate; perfluorobutanesulfonyl azide In methanol; diethyl ether; water at 20℃; for 6h;	97%
With sodium azide; copper(ll) sulfate pentahydrate; trifluoromethylsulfonic anhydride; potassium carbonate In methanol; dichloromethane; water at 20℃; for 48h;	90%
With triflic azide; sodium hydrogencarbonate; copper(II) sulfate In methanol; toluene at 20℃; for 14h;	52%

Upstream product

• 17996-12-2 N-benzyloxycarbonyl-6-amino-1-hexanol 
• 20395-28-2 5-chloropentyl acetate 
• 1345959-35-4 4-((6-hydroxyhexylcarbamoyloxy)methyl)-1-methylpyridinium trifluoromethanesulfonate 
• 629-11-8 1,6-hexanediol 
• 124-09-4 1,6-Hexanediamine 
• 34957-71-6 6-acetoxy-hexanenitrile 
• 371-34-6 ethyl 6-aminohexanoate 
• 111-49-9 hexamethylene imine 
• 105-60-2 caprolactam 
• 821-09-0 n-Pent-4-enyl alcohol 
• 201230-82-2 carbon monoxide 
• 100-46-9 benzylamine 
• 88910-22-9 5-hydroxymethylfuran-2-ylmethylamine 
• 163361-15-7 N-CO₂CH₃-6-amino-1-hexanol 

Downstream Products

• 18917-30-1 6-(7(9)H-purin-6-ylamino)-hexan-1-ol 
• 118686-42-3 2-methyl-4,5,6,7,8,9-hexahydro-[1,3]oxazonine 
• 101881-25-8 Phenyl-phosphonsaeure-di-(6-amino-hexyl)-ester 
• 40248-34-8 6-trifluoroacetamido-1-hexanol 
• 21524-98-1 4-Amino-salicylsaeure-(6-amino-hexylester) 
• 103268-05-9 6-Hydroxy-hexylimino-bis- 
• 102176-37-4 <4-Chlor-phenyl>-phosphonsaeure-di-(6-amino-hexyl)-ester 
• 17996-12-2 N-benzyloxycarbonyl-6-amino-1-hexanol 
• 97798-40-8 N-(6-hydroxyhexyl)benzamide 
• 125674-95-5 4-Nitrophenyl 3-[6-(4,4'-dimethoxytrityloxy)-hexylcarbamoyl]propanoate 
• 63945-11-9 6-phthalimido-1-hexanol 
• 23363-92-0 6-acetamido-1-hexanol 
• 92143-51-6 6-<(4-Azidobenzoyl)amino>-1-hexanol 
• 118355-37-6 (S)-2-Acetylamino-N-(6-hydroxy-hexyl)-3-phenyl-propionamide 

Relevant articles and documents

Sequential hydroaminomethylation/Pd-catalyzed hydrogenolysis as an atom efficient route to valuable primary and secondary amines

The facile synthesis of valuable primary and secondary amines is reported using a sequential procedure of hydroaminomethylation and Pd-catalyzed hydrogenolysis. The hydroaminomethylation reaction was catalyzed by a cationic Rh(I) iminopyridyl complex and the N-alkylated benzylamines were produced with high chemoselectivity, albeit as mixtures of linear and branched products. Performing the hydrogenolysis reaction using 10% Pd/C, provided access to valuable primary and secondary amines which have applications in the surfactant, pharmaceutical and polymer industries.

Method for preparing aliphatic amine compound

The invention discloses a method for preparing an aliphatic amine compound, comprising the following steps: using furfuryl amine or a furfuryl amine derivative as a raw material, and carrying out hydrogenolysis in the presence of a supported metal catalyst to obtain the aliphatic amine compound. According to the method disclosed by the invention, the aliphatic amine compound is prepared by catalyzing hydrogenolysis of the biomass-based furfuryl amine and the derivative thereof for the first time. The catalyst has high activity and high product selectivity. According to the method, a biomass-based compound is used as a raw material to prepare the aliphatic amine compound, and the requirements of sustainable development and green chemistry are met. The aliphatic amine compound prepared by the method has high selectivity, and is convenient for separation and purification of products. After the reaction of the method is finished, the catalyst is easy to separate and can be recycled, so that the method has a good application prospect.

Synthetic method 6-amino-1-hexanol

The invention discloses a synthetic method 6-amino-1-hexanol. According to the synthetic method 6-amino-1-hexanol, chlorosulphonyl isocyanate and 1, 6-hexanediol are taken as main raw materials, one-pot method is adopted to synthesize 6-amino-1-hexanol. The synthesis route comprises following steps: 1, under the catalyst effect of a tertiary amine, chlorosulphonyl isocyanate and a primary alcoholare reacted to generate a Burgess reagent, 1, 6-hexanediol is added to generate an intermediate 6-hydroxyhexyl carbamic acid; and 2, the intermediate 6-hydroxyhexyl carbamic acid synthesized in step is subjected to projecting group removing directly without separation so as to obtain target product 6-amino-1-hexanol. The synthetic method is low in cost, simple in reaction conditions, few in reaction steps, short in time, and high in purity and yield of finished product 6-amino-1-hexanol.