3452-97-9|3,5,5-Trimethylhexan-1-ol| Ambeed

CAS No. :	3452-97-9
Formula :	C₉H₂₀O
M.W :	144.25
SMILES Code :	CC(C)(C)CC(C)CCO
MDL No. :	MFCD00036138
InChI Key :	BODRLKRKPXBDBN-UHFFFAOYSA-N
Pubchem ID :	18938

Safety of [ 3452-97-9 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H302-H313-H315-H319-H360-H373-H401-H227
Precautionary Statements:	P501-P273-P260-P270-P202-P210-P201-P264-P280-P302+P352-P370+P378-P312-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330-P403+P235-P405
Class:	9
UN#:	3082
Packing Group:	Ⅲ

Computational Chemistry of [ 3452-97-9 ] Show Less

Physicochemical Properties

Num. heavy atoms	10
Num. arom. heavy atoms	0
Fraction Csp3	1.0
Num. rotatable bonds	4
Num. H-bond acceptors	1.0
Num. H-bond donors	1.0
Molar Refractivity	46.28
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	20.23 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.47
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	2.96
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.44
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	2.54
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	2.08
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.5

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.34
Solubility	0.667 mg/ml ; 0.00462 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-3.05
Solubility	0.129 mg/ml ; 0.000896 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-2.14
Solubility	1.04 mg/ml ; 0.00721 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-5.08 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	2.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.81

Application In Synthesis of [ 3452-97-9 ]

* 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 [ 3452-97-9 ]

[ 3452-97-9 ] Synthesis Path-Downstream 1~55

1
[ 79-14-1 ]
[ 3452-97-9 ]
glycolic acid-(3,5,5-trimethyl-hexyl ester) [ No CAS ]

References: [1]Industrial and Engineering Chemistry,1949,vol. 41,p. 2861.

2
[ 110-94-1 ]
[ 3452-97-9 ]
glutaric acid bis-(3,5,5-trimethyl-hexyl ester) [ No CAS ]

References: [1]Journal of Physical Chemistry,1955,vol. 59,p. 1097,1099.

3
[ 124-04-9 ]
[ 3452-97-9 ]
[ 20270-50-2 ]

References: [1]Industrial and Engineering Chemistry,1953,vol. 45,p. 1766,1769.

4
[ 111-20-6 ]
[ 3452-97-9 ]
[ 74347-07-2 ]

References: [1],1951,vol. 3891.
[2],1951,vol. 3891.
[3]Industrial and Engineering Chemistry,1949,vol. 41,p. 2861.

5
[ 139-13-9 ]
[ 3452-97-9 ]
nitrilotri-acetic acid tris-(3,5,5-trimethyl-hexyl ester) [ No CAS ]

References: [1]Industrial and Engineering Chemistry,1949,vol. 41,p. 2861.

6
[ 3452-97-9 ]
[ 420-05-3 ]
allophanic acid-(3,5,5-trimethyl-hexyl ester) [ No CAS ]

References: [1]Journal of the American Chemical Society,1950,vol. 72,p. 5342.

7
[ 3452-97-9 ]
[ 557-40-4 ]
[ 89585-64-8 ]

References: [1]Patent: US2847478,1956, .

8
[ 3452-97-9 ]
[ 62061-45-4 ]
(2,4,4-trimethyl-pent-1-enyl)-phosphonic acid bis-(3,5,5-trimethyl-hexyl ester) [ No CAS ]

References: [1]Patent: DE929207,1951, .

9
[ 3452-97-9 ]
[ 623163-66-6 ]

References: [1]Journal of the Chemical Society,1953,p. 2795.

10
[ 3452-97-9 ]
[ 52598-12-6 ]

References: [1]Industrial and Engineering Chemistry,1949,vol. 41,p. 2861.
[2]Industrial and Engineering Chemistry,1949,vol. 41,p. 2861.

11
[ 3452-97-9 ]
[ 72386-53-9 ]

References: [1]Patent: US2650908,1951, .

Yield	Reaction Conditions	Operation in experiment
		Examples of organoleptic alcohols and phenols include:amyl alcohol...3-methyl-but-2-en-1-ol3-methyl-1-pentanolcis-3-hexenolcis-4-hexenol3,5,5-trimethyl hexanol3,4,5,6,6-pentamethylheptan-2-olcitronellolgeraniol...
		Non-limiting examples of alcohols generated from the compounds of the present invention include primary, secondary and tertiary alcohols and phenols such as:amyl alcohol;...3-methyl-but-2-en-1-ol;3-methyl-1-pentanol;cis-3-hexenol;cis-4-hexenol;3,5,5-trimethyl-hexanol;3,4,5,6,6-pentamethylheptan-2-ol;citronellol;geraniol;...
		Examples of organoleptic monoalcohols and phenols constituting the residue R- in the compounds of formula I and generated upon cleavage are:amyl alcohol...3-methyl-but-2-en-1-ol3-methyl-1-pentanolcis-3-hexenolcis-4-hexenol3,5,5-trimethyl hexanol3,4,5,6,6-pentamethylheptan-2-olcitronellolgeraniol...

Compounds of formula I may generate the following alcohols and phenols:amyl alcohol...3-methyl-but-2-en-1-ol*3-methyl-1-pentanolcis-3-hexenol*cis-4-hexenol*3,5,5-trimethyl-hexanol3,4,5,6,6-pentamethylheptan-2-ol*citronellol*geraniol*...

13
[ 3452-97-9 ]
[ 50915-80-5 ]

Yield	Reaction Conditions	Operation in experiment
78%	With sulfuric acid; hydrogen bromide; In water; at 120℃; for 5h;	Specifically, 3,5,5-trimethyl hexanol 70g and 47percent bromide bromine aqueous solutionand 84g and sulfuric acid 16g to 5 hours at 120 .Hexane was added to the obtained reaction solution, washed with water three times, and then hexane was distilled off to obtain 3,5,5-trimethyl-1-bromohexane (78 molpercent).

References: [1]Journal of the American Chemical Society,2008,vol. 130,p. 17212 - 17213.
[2]Patent: JP2016/175882,2016,A .Location in patent: Paragraph 0044; 0045.
[3]Journal of the Chemical Society,1952,p. 1761.
[4]Journal of the Chemical Society,1951,p. 2064,2066.
[5]Reactive and functional polymers,2015,vol. 86,p. 67 - 79.
[6]Journal of Materials Chemistry C,2018,vol. 6,p. 11980 - 11991.

14
[ 3452-97-9 ]
[ 4316-65-8 ]

References: [1]Recueil des Travaux Chimiques des Pays-Bas,1948,vol. 67,p. 302.

15
[ 3452-97-9 ]
[ 3378-75-4 ]

References: [1]Patent: US2644834,1950, .
[2]Industrial and Engineering Chemistry,1949,vol. 41,p. 2861.
[3]Patent: DE832147,1950, .
DRP/DRBP Org.Chem.,.

16
[ 3452-97-9 ]
[ 5435-64-3 ]

References: [1]Industrial and Engineering Chemistry,1949,vol. 41,p. 2861.
[2]Industrial and Engineering Chemistry,1949,vol. 41,p. 2861.
[3]Organic Process Research and Development,2019,vol. 23,p. 1709 - 1717.

17
[ 3452-97-9 ]
[ 3302-10-1 ]

References: [1]Journal of the Chemical Society,1951,p. 2543.
[2]Industrial and Engineering Chemistry,1949,vol. 41,p. 2861.
[3]Organic Process Research and Development,2019,vol. 23,p. 1709 - 1717.

18
[ 3452-97-9 ]
[ 36400-98-3 ]

Yield	Reaction Conditions	Operation in experiment
100%	With 3,5,5-trimethyl hexanal; hydrogen; zinc(II) oxide; at 230℃; for 5h;Catalytic behavior;	A 100 mL flask equipped with a condenser packed at the bottom with MS4A was charged with 25.7 g of TMHOL as the starting material, 1.00 g (10 mol percent with respect to the starting material) of potassium hydroxide (KOH) (granular; guaranteed reagent from Wako Pure Chemical Industries, Ltd.; purity, ?85percent) as the base, and 2.5 g (9.9 mol percent with respect to the starting material) of TMHAL as the catalyst. Next, the mixture was reacted for 5 hours in an oil bath set to 230° C. while blowing (bubbling) 0.1 L/min of hydrogen gas (compressed hydrogen gas, from Toho Sakata Suiso KK) into the mixture under stirring. The mixture was then cooled to room temperature (about 23° C.), and the blowing of hydrogen gas was stopped. The product peak retention time was confirmed by GC to agree with the retention time for the reference material. The peak portion was then analyzed by GC-MS, and the molecular weight and degradation product pattern were confirmed to agree with those for the reference material. The reaction product obtained was the target substance 2-(4,4-dimethylpentan-2-yl)-5,7,7-trimethyl-1-octanol, and the yield was 90.5percent. As used herein, the ?yield? means the ratio of the amount of target product actually obtained to the amount of target product that can be obtained from the entire charged amount of the starting material, and is a value determined by the following formula. Yield (percent)=amount of target product (mol)/amount of starting material charged (mol)×2×100

References: [1]Patent: US10179755,2019,B2 .Location in patent: Page/Page column 6; 7; 8.
[2]Industrial and Engineering Chemistry,1949,vol. 41,p. 2861.

19
[ 3452-97-9 ]
[ 148286-83-3 ]

References: [1]Journal of the Chemical Society,1953,p. 2795.
[2]Journal of the Chemical Society,1953,p. 2795.

20
[ 3452-97-9 ]
phosphoric acid diphenyl ester-(3,5,5-trimethyl-hexyl ester) [ No CAS ]

References: [1]Industrial and Engineering Chemistry,1954,vol. 46,p. 208.

21
[ 3452-97-9 ]
[ 42202-03-9 ]

References: [1]Journal of the Chemical Society,1951,p. 2064,2066.
[2]Industrial and Engineering Chemistry,1949,vol. 41,p. 2861.

22
[ 3452-97-9 ]
[ 96-97-9 ]
[ 155388-66-2 ]

References: [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 845 - 859.

23
[ 3452-97-9 ]
[ 135696-94-5 ]
[ 135696-78-5 ]

References: [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 539 - 547.

24
[ 3452-97-9 ]
[ 917831-75-5 ]

References: [1]European Journal of Inorganic Chemistry,2006,p. 1067 - 1075.

25
[ 3452-97-9 ]
[ 644-97-3 ]
[ 63592-57-4 ]

References: [1]European Journal of Inorganic Chemistry,2006,p. 1067 - 1075.

26
[ 3452-97-9 ]
[ 1079-66-9 ]
[ 917831-78-8 ]

References: [1]European Journal of Inorganic Chemistry,2006,p. 1067 - 1075.

27
[ 110-87-2 ]
[ 3452-97-9 ]
2-(3,5,5-trimethyl-hexyloxy)-tetrahydro-pyran [ No CAS ]

References: [1]Synthetic Communications,2006,vol. 36,p. 2893 - 2900.

28
[ 110-52-1 ]
[ 3452-97-9 ]
[ 102547-12-6 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; tetrabutylammomium bromide; In water;	Preparation Example 2 Into a 2 liter glass flask, 317 g of <strong>[3452-97-9]3,5,5-trimethylhexanol</strong>, 216 g of 1,4-dibromobutane, 14.3 g of tetrabutylammonium bromide and 442 g of a 52percent by mass aqueous solution of sodium hydroxide were placed, and the reaction was allowed to proceed at 70° C. for 8 hours under stirring. After the reaction was completed, the reaction mixture was transferred to a separatory funnel, and the aqueous phase was removed by filtration. The remaining organic phase was washed with 500 ml of water 5 times. From the organic phase, 1,4-bis(3,5,5-trimethylhexoxy)butane was separated by distillation under a reduced pressure.

References: [1]Patent: US2007/281873,2007,A1 .

29
[ 3452-97-9 ]
N^α,N^α'-oxalyl-bis(N^ε-lauroyl-L-lysine 3,5,5-trimethylhexyl ester) [ No CAS ]

References: [1]Organic and biomolecular chemistry,2003,vol. 1,p. 4124 - 4131.

30
[ 3452-97-9 ]
silver contact [ No CAS ]
[ 154737-82-3 ]

References: [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 845 - 859.

31
[ 3452-97-9 ]
silver contact [ No CAS ]
2-hydroxy-5-{N-[(2,5-dihydroxyphenyl)methylidene]amino}benzoic acid 3,5,5-trimethylhexyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 845 - 859.

32
[ 3452-97-9 ]
silver contact [ No CAS ]
5-(2,5-Dihydroxy-benzylamino)-2-hydroxy-benzoic acid 3,5,5-trimethyl-hexyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 845 - 859.

33
[ 3452-97-9 ]
[ 14103-61-8 ]

References: [1]Journal of the Chemical Society,1953,p. 2795.

34
[ 3452-97-9 ]
[ 859995-32-7 ]

References: [1]Journal of the Chemical Society,1951,p. 2543.

35
[ 3452-97-9 ]
[ 3035-75-4 ]

References: [1]Journal of the Chemical Society,1951,p. 2064,2066.

36
[ 3452-97-9 ]
[ 150150-19-9 ]

References: [1]Journal of the Chemical Society,1951,p. 2543.

37
[ 3452-97-9 ]
[ 3378-63-0 ]

References: [1]Industrial and Engineering Chemistry,1949,vol. 41,p. 2861.

38
[ 3452-97-9 ]
[ 98958-13-5 ]

References: [1]Industrial and Engineering Chemistry,1949,vol. 41,p. 2861.

39
[ 3452-97-9 ]
[ 775352-42-6 ]

References: [1]Journal of the Chemical Society,1951,p. 2543.

40
[ 3452-97-9 ]
[ 2570-95-8 ]

References: [1]Journal of the Chemical Society,1951,p. 2064,2066.

41
[ 3452-97-9 ]
[ 106652-67-9 ]

References: [1]Industrial and Engineering Chemistry,1949,vol. 41,p. 2861.

42
[ 3452-97-9 ]
[ 106593-67-3 ]

References: [1]Journal of the Chemical Society,1951,p. 2064,2066.

43
[ 3452-97-9 ]
[ 90726-43-5 ]

References: [1]Industrial and Engineering Chemistry,1949,vol. 41,p. 2861.

44
[ 3452-97-9 ]
3,5,5-trimethyl-hexylsulfanyl cyanate [ No CAS ]

References: [1]Industrial and Engineering Chemistry,1949,vol. 41,p. 2861.

45
[ 3452-97-9 ]
[ 103754-97-8 ]

References: [1]Journal of the Chemical Society,1951,p. 2064,2066.

46
[ 3452-97-9 ]
[ 67707-75-9 ]

References: [1]Journal of the Chemical Society,1951,p. 2543.

47
[ 3452-97-9 ]
[ 6284-82-8 ]

References: [1]Industrial and Engineering Chemistry,1949,vol. 41,p. 2861.

48
[ 3452-97-9 ]
[ 773157-31-6 ]

References: [1]Journal of the Chemical Society,1951,p. 2543.

49
[ 3452-97-9 ]
[ 857078-64-9 ]

References: [1]Journal of the Chemical Society,1951,p. 2064,2066.

50
[ 3452-97-9 ]
[ 55255-73-7 ]

References: [1]Journal of the Chemical Society,1951,p. 2064,2066.

51
[ 3452-97-9 ]
[ 94376-47-3 ]

References: [1]Industrial and Engineering Chemistry,1949,vol. 41,p. 2861.

52
[ 3452-97-9 ]
[ 36727-29-4 ]

References: [1]Industrial and Engineering Chemistry,1949,vol. 41,p. 2861.
[2]Journal of the Chemical Society,1951,p. 2543.

53
[ 3452-97-9 ]
[ 16747-26-5 ]

References: [1]Journal of the Chemical Society,1952,p. 1761.

54
[ 5435-64-3 ]
[ 3452-97-9 ]

Yield	Reaction Conditions	Operation in experiment
74%	With formic acid; water; palladium diacetate; tricyclohexylphosphine; In 1,4-dioxane; at 90℃; for 6h;Inert atmosphere; Sealed tube;	General procedure: An oven-dried pressure tube containing a Teflon-coated stirring bar was charged with Pd(OAc)2 (11.2 mg, 5 molpercent), PCy3 (21 mg, 7.5 molpercent) and aldehyde(1 mmol).The tube was sealed, evacuated and backfilled with N2. 1 mL of dioxane was subsequently injected. After the mixture was stirred at room temperature for 15 min, H2O (180 mg, 10 equiv) and HCO2H (184 mg, 4 equiv) were injected and the reaction was heated to 90 oC for 18 h. After the reaction was completed, the solvent was removed under vacuo. The residues were purified by flash column chromatography on silica gel to afford 87 mg of benzyl alcohol in 81 percent yield.
	With thiophene; hydrogen;Pricat CZ 29/2T; at 300℃; under 150015.0 Torr; for 0 - 264h;	A laboratory scale hydrogenation of nonanal, which had been produced by the [HYDROFORMYLATION OF DI-ISOBUTENE,] was carried out using a microreactor containing a [10ML] sample of PRICAT CZ 29/2 (35 wtpercent copper oxide/65 wtpercent zinc oxide) catalyst. Nonanal consists predominantly (about 90percent by weight) of a single isomer, which is 3,5, 5- [TRIMETHYLHEXANAL.] The catalyst was reduced in the micro reactor at atmospheric pressure and [250 °C] in a hydrogen-containing nitrogen stream flowing at 1 I/hr. the concentration of hydrogen in the gas stream was increased from 5percent to 100percent over a period of about 10 hours. The reactor was then brought up to operating pressure (200 barg) using neat hydrogen. The reactor was then operated at 300 [°C] at a gas: oil ratio of 7923: 1, using the nonanal feed at a liquid feed rate of 15-20 [ML/HOUR] to show the performance of the catalyst before treatment with the sulphur compound. The gas: oil ratio is the hydrogen flow rate [(RM3/HR,] i. e. measured at [20 °C] and 1 atmosphere) divided by the liquid feed rate (m3/hr). 0.2 ml of thiophene was then added to the feed vessel contents (1.9 litres) and the reactor was run continuously under the same conditions until the feed had been consumed (7 days). Subsequently the reactor was run using aldehyde feed containing no thiophene. The feed and product streams were analysed using temperature-programmed capillary gas chromatography. Table 1 shows the concentration of the major components in the feed stream and in the product stream over the course of the reaction. The abbreviations used in the table are: 244 tmp: 2,4, 4-trimethyl pentane 224 tmh: 2,2, 4-trimethyl hexane aldehyde: 3,5, [5-TRIMETHYLHEXANAL] alcohol : 3,5, 5-trimethylhexanol heavies: heavy end products including dimer (C18) ester, dimer alcohol, dimer ether, trimers and other high boiling by products. Table 1 Day 244tmp 224tmh Aldehyde Alcohol Heavies (Feed) 2. 4 0. 1 85. 4 8. 5 0. 58 0 3. 3 16. 2 0. 1 75. 9 4. 66 1 3. 6 9. 1 0. 1 81. 7 7. 25 2 3. 2 2. 7 0. 2 89. 8 6. 91 3 3. 4 1. 8 0. 4 89. 8 6. 85 4 3. 0 1. 7 0. 4 90. 2 7. 07 5 2. 6 2. 3 0. 3 90. 1 7. 5 6 2. 9 2. 6 0. 3 89. 9 6. 92 7 2. 5 2. 6 0. 3 90. 1 7. 21 8 2. 7 2. 7 0. 3 89. 9 7 9 2. 2 2. 3 0. 3 92. 3 4. 38 10 2. 7 2. 5 0. 3 91. 8 3. 78 11 2. 9 2. 7 0. 3 90. 3 5. 03 There is very little unhydroformylated olefin in the crude aldehyde product used in this example. The concentration of 2,4, 4-trimethyl pentane, which would be the product of hydrogenating di-isobutene is relatively low and constant. However, the concentration of 2,2, 4-trimethyl hexane, which is at a very low level in the feed rises to over 16percent when the hydrogenation takes place over un-treated catalyst. 2,2, 4-trimethyl hexane is present as a product of the hydrogenolysis of the product alcohol. It is very noticeable that during and after treatment with thiophene, the concentration of 2,2, 4-trimethyl hexane falls to about 2.5percent with a corresponding increase in the concentration of desired product alcohol in the product stream.
	With hydrogen;Cu/Cr/Ni catalyst; at 180℃; under 18751.9 Torr;	Example 3 Preparation of 3,5,5-trimethylhexyl Benzoate (Comparative Example) 1000 g of 2,4,4-trimethyl-1-pentene (diisobutene) from Oxeno (may be prepared as in DE 10106593.0, for example) were hydroformylated in a 2 l autoclave at 135° C. under 270 bar of synthesis gas pressure for 3 hours in the presence of an unmodified rhodium catalyst.The active catalyst was generated in situ from rhodium nonanoate (24.8percent by weight of Rh).rhodium concentration based on diisobutene was set at 20 ppm. After 3 hours the reaction was terminated and the autoclave was cooled to 20° C. The reaction discharge comprises 93.5percent by weight of 3,5,5-trimethylhexanal, 2.5percent by weight of 3,5,5-trimethylhexanol, 3.4percent by weight of residual C8 hydrocarbons, and 0.6percent by weight of high-boilers. The reaction discharge was freed from rhodium catalyst by distillation on a laboratory distillation column. The Rh-free hydroformylation discharge was then hydrogenated in the liquid phase in a fixed-bed reactor in the presence of a Cu/Cr/Ni catalyst at 180° C. and 25 bar. After hydrogenation of 3,5,5-trimethylhexanal to give the target product 3,5,5-trimethylhexanol, the hydrogenation discharge was freed from low-boilers (C8 hydrocarbons) by controlled distillation. [0071] The distillation process gave a 3,5,5-trimethylhexanol of purity above 99.5percent by weight.

References: [1]Synthetic Communications,2014,vol. 44,p. 280 - 288.
[2]Patent: WO2004/26800,2004,A1 .Location in patent: Page 5; 6.
[3]Patent: US2004/15007,2004,A1 .Location in patent: Page 5.
[4]Patent: WO2006/136471,2006,A1 .Location in patent: Page/Page column 25-26.
[5]Organic Letters,2019,vol. 21,p. 2693 - 2698.

55
[ 107-39-1 ]
synthesis gas [ No CAS ]
[ 3452-97-9 ]
[ 5435-64-3 ]

Yield	Reaction Conditions	Operation in experiment
	rhodium nonanoate; at 135℃; under 202520.0 Torr; for 3h;	Example 3 Preparation of 3,5,5-trimethylhexyl Benzoate (Comparative Example) 1000 g of 2,4,4-trimethyl-1-pentene (diisobutene) from Oxeno (may be prepared as in DE 10106593.0, for example) were hydroformylated in a 2 l autoclave at 135° C. under 270 bar of synthesis gas pressure for 3 hours in the presence of an unmodified rhodium catalyst.The active catalyst was generated in situ from rhodium nonanoate (24.8percent by weight of Rh).rhodium concentration based on diisobutene was set at 20 ppm. After 3 hours the reaction was terminated and the autoclave was cooled to 20° C. The reaction discharge comprises 93.5percent by weight of 3,5,5-trimethylhexanal, 2.5percent by weight of 3,5,5-trimethylhexanol, 3.4percent by weight of residual C8 hydrocarbons, and 0.6percent by weight of high-boilers. The reaction discharge was freed from rhodium catalyst by distillation on a laboratory distillation column.

References: [1]Patent: US2004/15007,2004,A1 .Location in patent: Page 5.

Historical Records

Technical Information

• Appel Reaction • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chugaev Reaction • Corey-Kim Oxidation • Dess-Martin Oxidation • Heat of Combustion • Hydride Reductions • Jones Oxidation • Martin's Sulfurane Dehydrating Reagent • Mitsunobu Reaction • Moffatt Oxidation • Oxidation of Alcohols by DMSO • Preparation of Alcohols • Preparation of Amines • Reactions of Alcohols • Reactions with Organometallic Reagents • Ritter Reaction • Sharpless Olefin Synthesis • Swern Oxidation

Related Functional Groups of
[ 3452-97-9 ]

Aliphatic Chain Hydrocarbons

A109714 [38514-05-5]

6-Methyloctan-1-ol

Similarity: 0.92

A280873 [624-95-3]

3,3-Dimethylbutan-1-ol

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A158426 [32444-34-1]

2-Ethyl-3-methylbutan-1-ol

Similarity: 0.85

A264125 [5333-42-6]

2-Octyldodecan-1-ol

Similarity: 0.85

A329783 [108-82-7]

2,6-Dimethylheptan-4-ol

Similarity: 0.79

Alcohols

A109714 [38514-05-5]

6-Methyloctan-1-ol

Similarity: 0.92

A280873 [624-95-3]

3,3-Dimethylbutan-1-ol

Similarity: 0.92

A223157 [770-71-8]

Adamantan-1-ylmethanol

Similarity: 0.86

A357021 [826-45-9]

Bicyclo[2.2.2]octane-1,4-diyldimethanol

Similarity: 0.86

A264125 [5333-42-6]

2-Octyldodecan-1-ol

Similarity: 0.85

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
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
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P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
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:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
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P308	IF exposed or concerned:
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P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
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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.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
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.
P381	Eliminate all ignition sources if safe to do so.
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.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
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.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
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
H271	May cause fire or explosion; strong oxidizer
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
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
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
H350	May cause cancer
H351	Suspected of causing cancer
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.: 3452-97-9

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CAS No.: 3452-97-9

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CAS No.: 3452-97-9

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CAS No.: 3452-97-9

Alternative Products

Product Details of [ 3452-97-9 ]

Safety of [ 3452-97-9 ]

Computational Chemistry of [ 3452-97-9 ] Show Less

Physicochemical Properties

Lipophilicity

Water Solubility

Pharmacokinetics

Druglikeness

Medicinal Chemistry

Application In Synthesis of [ 3452-97-9 ]

[ 3452-97-9 ] Synthesis Path-Downstream 1~55

Related Products

Historical Records

Technical Information

Categories

Related Functional Groups of [ 3452-97-9 ]

Aliphatic Chain Hydrocarbons

Alcohols

Precautionary Statements-General

Prevention

Response

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Physical hazards

Health hazards

Environmental hazards

Inquiry

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Related Functional Groups of
[ 3452-97-9 ]